⏰ Today in 5 Minutes or Less

Discover why tech leaders are migrating to enterprise SaaS to escape AI layoffs, the hidden operational friction waiting for them, and how to successfully pivot from a tactical "feature factory" to a strategic partner.

The Illusion of the Safe Harbor: When Day 1 Demands a New Floor

You’ve just been headhunted into a high-level executive role at a major enterprise SaaS firm. The mandate is a leader's dream: scale design maturity, spearhead product evolution, and capture market dominance.

In an era defined by AI fatigue, quiet layoffs, and shrinking tech roles, B2B enterprise SaaS looks like the ultimate safe harbor. You step into the office on Day 1, primed to align world-class product design with macro business metrics.

Then reality hits.

Behind a highly profitable business model lies an internal organization missing the foundational mechanics of modern product delivery. There are no standardized hiring protocols, no talent acquisition partners who actually understand design, and zero baseline job architecture. Instead, you're left holding the bag with a legacy team and a patchwork of talent unequipped for the realities of a complex enterprise ecosystem.

You realize the bitter truth: Before you can scale the future, you have to engineer the floor.

"I'm building the plane as we fly it. People are asking me what the team is going to look like, and honestly, I'm still figuring out if we even have the right parts."

🚧 My Own Bumpy Road: From Tech to SaaS

I know this whiplash intimately because I lived it.

When I left the consumer-facing worlds of Apple and Yahoo! to step into my first role as Chief Design Officer at an enterprise SaaS company, I thought I was fully equipped. I brought decades of top-tier design pedigree, user centered design process, design frameworks, career paths and a clear vision of what world-class product design looked like.

But consumer tech playbooks don't map cleanly onto complex B2B ecosystems.

My first 18 months were a  trial by fire. Nothing was in place and everything had to be built from scratch. Yet, looking back, it became one of the most rewarding roles I’ve ever had.

The friction was real, but the impact was monumental. If you are considering or currently navigating this exact migration to escape the volatility of tech, understand that the grass isn't always greener, the transition is bumpy, but the payoff is unmatched because you can see what you created, the value it brought to the business and most importantly the amazing teams of people you hire to help you get there.

The Reality of the SaaS Enterprise Shift

When we look at the leaders navigating this migration today, the experience is defined by three distinct dynamics:

• The Stability Trade-Off: Trading consumer tech volatility for enterprise scale means inheriting a completely different kind of exhaustion: deep institutional inertia and ignorance about how user informed, data driven product design methods drive the bottom line.

• The Domain Fluency Barrier: In enterprise SaaS, you are dealing with massive, deeply complex workflows, legacy technical debt, and highly specialized user bases. Tech playbooks won't work out of the box; a major hurdle is translating complex business logic into design solutions and from here into scalable design frameworks. 

• Political Capital vs. Elite Credentials: Your top-tier tech pedigree and resume mean very little on Day 1 in an enterprise. To be heard, you must slow down, learn the specific nuances of the business and its executives, and build cross-functional relationships across sales, human resources, data science, business development, operations, customer service, marketing, engineering, and product management.

• The High-Risk Alternative: Alternatively, you can do what I did, though it is highly inadvisable. I stepped back into the trenches as both the hands-on designer and the strategist, throwing everything I had into securing a major, immediate commercial win for the company. While this builds professional capital to reach, it carries a massive risk: you have to ensure you don't burn the very relationships you need to build in the process or burn yourself out in the process of trying.

🏭 The Strategic Trap: Feature Factory or Strategic Partner?

This foundational chaos brings a massive strategic risk for a product design leader. In enterprise SaaS, if you are not careful, the organization will default to treating your team as a servant function rather than a strategic partner.

When solution and sales-driven organizations see a gap in execution or capability, their immediate reaction is to drag design down to the purely tactical layer, treating your team like an internal production agency tasked with quickly mocking up features to close an individual client deal. Whilst it's hard to say no to work, you need to diagnose this dynamic quickly. 

The Servant Dynamic (The 'Ticket-Taker' Trap): Is your team trapped in an operational ticket queue, responding to one-off sales requests, and executing on pre-determined feature roadmaps?

"Hey, we've decided on the new feature for the enterprise dashboard. Can you get us some wireframes and high-fidelity mocks by Friday? We need to ship this before the next sprint."

If you dive straight into fixing every tactical emergency yourself, something I term ‘skill gapping’, you implicitly validate the "servant" model. You inadvertently teach the company that your value lies in output velocity, keeping your team locked in a reactive loop.

The Partner Dynamic (The 'Strategic Pivot'): Are you positioned cross-functionally across organizational pillars to shape product strategy, map business context, and co-own systemic outcomes that drive retention and expansion?

"Hey, the enterprise team is struggling to keep our larger accounts from churning. We're looking at the data, and it seems like the onboarding complexity is the main friction point. I’d love your take on the business context here. How should we be architecting this experience to improve retention?”

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🚚 How to Drive Integration and Find the Reward

While the transition is filled with friction, the payoff of successfully transforming an enterprise SaaS engine is massive. You are restructuring how a high-impact business operates. If you are finding yourself stuck, here are some ideas to help you get back into the flow.

• Shield the Core with External Support: If stakeholders demand immediate tactical design polish or sales collateral before your internal team is properly hired or leveled up, pull over the external budget to handle the noise. Protect your internal team's focus so they can design the core product architecture.

• Educate Upward and Outward: Map out product designs job architecture for your cross-functional peers. Accept that "they don't know what they don't know." Educate them on how product design and user research directly impact product adoption and reduce churn, not just how they make the software look pretty.

• Own the Medium-Term Blueprint: Recognize that shoring up a weak team foundation and establishing a durable product design practice takes time. So don’t allow short-term operational chaos to distort your long-term value proposition.

🔥 The Short Of It Is

• The Safe Harbor Has a Price: Moving to enterprise SaaS protects you from the immediate volatility of tech and AI layoffs, but you trade that chaos for deep institutional inertia and complex domain architectures.

• Build the Floor First: Your consumer tech credentials won't save you on Day 1. Anticipate spending your first several months building foundational job architectures, recruitment pipelines, and baseline operational structures.

• Shift the Altitude: Avoid the strategic trap of letting sales-driven teams treat design as a servant function. Educate upward, protect your core team with external support, and focus on long-term business metrics like retention and churn over quick feature outputs.

You weren't hired to be a pair of hands; you were hired to change the altitude of the function. Shift the conversation away from tactical outputs, and remind the business why they brought an expert in to build the foundation in the first place.

Until next week,

Sally

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

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• Subscribe to, or share this Newsletter with a friend

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Related Newsletters

• How to Instantly Prove Your Worth in a Tech Leadership Role: Learn the playbook for turning design strategy into measurable business success.

• The Design Leader's Ascent: A Strategic Guide to Navigating Your First 10 Years and Beyond.

With ❤️ from Sally

⏰ Today in 5 Minutes or Less

"Head of Design" sounds prestigious. It carries the promise that you’re finally steering the ship moving past execution and into true strategy.

But let’s be completely honest: it’s often just packaged corporate gaslighting.

It’s a title designed to flatter your ego while actively capping your power. The organization demands the structural accountability of a VP and the strategic scope of a Director, but hands you the budget of a mid-level manager.

Ask yourself: Are you actually leading, or are you just a shield for executive failure?

Let’s unpack the anatomy of this trap, and why this setup is a ticking time bomb for your career.

😏 The Illusion of Ownership

In many tech companies, "Head of Design" is a convenient parking place. It allows the organization to brag that they "value design," while structurally ensuring that design remains subservient to another division. If you report to Marketing, Engineering, or Product, you aren't partnering with them, you are being managed by them.

✅ The Pros: The Craft Sanctuary

• Freedom from Corporate Plumbing: Because you aren't a formal VP, you are mostly exempted from grueling, cross-functional fiscal battles and enterprise-level financial planning.

• Pure Design Focus: It keeps you closer to the actual craft, the team, and the immediate product experience. You get to build a design culture without being consumed by corporate administration.

• Love Being a Head of Design? If you’re entirely comfortable in your role, stop reading right now. You won't like what comes next. You might believe this doesn’t apply to you, or that your company is the rare exception where this would never happen. But if you have that nagging, quiet feeling that your strategic runway is getting shorter by the day, please keep scrolling.

❌ The Cons: The Dilution Matrix

• Responsibility Without Resource: You own design output, the quality, and the team's morale, but your operational budget belongs to someone else. You have to ask permission to hire, scale, or buy tooling.

• Business Blindspots: Because you are structurally insulated from the core business machinery, your visibility into true company strategy is restricted. You aren't in the room where the financial trade-offs are actually made.

• Invisible Impact: When your team delivers a brilliant piece of work that shifts corporate metrics, the executive who owns the business function above you reaps the rewards, the visibility, and the equity allocation. Your hard work is converted directly into their political capital.

⚖️ The Scale and Acquisition Trap: Has This Happened to You?

If you took a "Head of Design" title at an early-stage startup, understand this: Because your title carries no corporate financial stake, your proximity to power is an illusion.

When the company is small, you are the founding design partner. But what happens when the Series A or B funding hits, or an acquisition loop begins?

Suddenly, outside investors arrive. They look at the org chart and demand "seasoned enterprise executives." Because you lack structural parity on paper, you are highly vulnerable.

Look at your career right now, or the peers around you: How many times have you seen a brilliant design leader reporting directly to the founders, only to find themselves post-investment or post-acquisition bumped two, three, or four levels down the organization?

As more senior people on paper are layered above you, the freedom and direct access you enjoyed is completely diminished. Access to power is removed, and you are left executing someone else's vision. If you’ve experienced this, or if you are watching the layers slowly build above you right now, tell me your story in the comments below. Let's expose how common this sequence really is.

When you are systematically removed from the seat of power, it’s not a transition, it's a clear signal that it's time to move on. You need a role that keeps you at the table when the money changes hands.

🔢 By The Numbers: The Title Landscape

How prevalent is this title? If you look at data across tech hubs like London and San Francisco, "Head of Design" typically accounts for roughly 12% to 15% of all senior design leadership postings.

But here is what the data won’t tell you: it is heavily skewed toward seed-stage to Series B startups, or legacy corporate environments trying to build a digital function from scratch. When an organization matures, they drop the "Head of" vagueness and use normal corporate hierarchy titles:

• The Director of Design: This is usually the truest equivalent of a functional "Head of." A Director owns a defined business line, holds explicit headcount budget, and has direct input into product roadmaps.

• The VP of Design: This is an executive officer role. A VP manages the design function and the business outcomes. They have a seat at the table with the peer VPs of Product and Engineering to co-author company strategy.

The Golden Rule of Titles: Does the title exist for any other function in the company? If the organization has a VP of Product and a VP of Engineering, but a Head of Design, they are telling you exactly where design sits in the hierarchy of power. It’s an immediate signal of structural asymmetry.

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5 Questions to Ask Before You Sign ❓❓❓❓❓

If you are looking at a Head of Design role, or trying to rescue the one you currently hold? You must audit the reality of the role before you sign your contract. Use these five questions to do your audit.

1. Check for cross-functional symmetry (The Peer Test)
   Are there "Head of" titles for Product, Engineering, or Marketing? Or do those functions report into VPs and Chiefs? If design is the only function given a "Head of" moniker, you are entering an asymmetrical relationship from Day 1.

2. Locate the financial baseline (The Budget Test)
   Do I have a direct, non-negotiable line of budget for headcount, tooling, and agencies? Or do I have to request budget allocation from another division's leader for approval?

3. Define the scope of ownership (The Accountability Test)
   What am I accountable for? Am I accountable solely for design execution and velocity, or am I accountable for core business health, revenue, or user retention metrics?

4. Map the reporting line (The Visibility Test)
   Who does this role report to, and who do they report to? If there are more than two layers between you and the CEO, your strategic impact will be systematically diluted before it ever reaches executive ears.

5. Evaluate the growth and scale roadmap (The Dilution Test)
   When the company raises its next round of investment or scales, what happens to this role? Is there a commitment to elevate this position to a VP/Director level to keep a seat at the table, or will new leadership layers be placed above it?

Advocating for Something Better

If you love the company but realize the title is a structural bottleneck, you have the right, and the strategic obligation to advocate for a reclassification before you accept.

Frame the shift from Head of Design to Director of Design not as an exercise in personal ego, but as a mechanism for organizational velocity.

Tell them: "To deliver the product quality and strategic alignment you are asking for, this role requires direct fiscal oversight and structural parity with Product and Engineering. Let's align the title to reflect that operational reality and ensure design keeps its seat at the table as we scale."

A title isn't just letters on a LinkedIn profile. It is the invisible API that dictates how much power, resource, and leverage you have to do the work you were hired to do. Choose yours wisely.

🚀 The Short Of It Is

• The "Head of" title is structurally rigged to demand executive accountability without giving you executive budget or power.

• Startups use it as a placeholder until outside funding arrives, at which point design leaders are routinely layered over and pushed down.

• Stop settling for ego-flattery. If they want you to run the function, demand structural parity, a direct budget line, and a Director or VP title.

• Have you been hit by the Scale and Acquisition Trap? Drop your experiences in the comments? Let’s talk about what really happens behind closed doors when the employment contract gets signed.

About the Author

Sally Grisedale is an executive coach, author and global user experience design leader. She has built, led and scaled world-class design teams inside Silicon Valley's most influential tech institutions including Apple, Meta and Yahoo, and has served as Chief Design Officer at startups steering corporate design strategy at scale. Today, she coaches the next generation of creative leaders on how to secure genuine organizational influence, survive high-pressure executive transitions, and protect their careers from structural gridlock. Learn more about her frameworks and executive coaching practices at sallygrisedale.com.

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or gift a copy of my book to your team

• Subscribe to, or share this Newsletter with a friend

• Chat with my AI assistant to learn more about how we could work together

Related Newsletters

Partner or Servant? Design Teams Working in Tech: A Complex Dance. The hidden architectural blueprints of tech organizations, and the structural relationships design teams hold within the larger corporate machinery. 

How Design Executives Secure Real Influence. Four real-world case studies on neutralizing executive panic, mastering safe pushback, and surviving high-pressure tech transitions

With ❤️ from Sally

Welcome to Leading by Design!

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💥 When a Coworker Becomes a Threat to Your Sanity

There is a specific kind of professional grief that occurs when you encounter someone who operates with a behavioral playbook you would never dream of using. It is the acute toxicity of a peer who doesn’t just disagree with your strategy, but actively attacks your integrity, mischaracterizes your intentions, and attempts to dismantle your standing in the organization.

When you are an authentic, relationship-driven leader, running into this type of brick wall causes profound unrest. Working with a coaching client last week who is currently being taken down by a cross-functional coworker put me right back in the pressure cooker. It triggered vivid memories of my own career in tech leadership.

This happened to me several times and on every occasion, I was completely blindsided, lacked the tools to protect myself, and felt the full weight of a peer trying to take me out Writing about this years later and with the benefit of hindsight, I can see the anatomy of these situations with absolute clarity. Back then, I spiraled.

Today, I can offer the playbook I needed when I was in those shoes. Looking back at my own experiences and what my client faced last week, the severe toll of corporate hostility follows a predictable pattern:

• The Physical and Nervous System Collapse: The stress doesn't stay at the office. It manifests as a hyper-activated nervous system, losing sleep, crying, and an inability to be present with family and friends because your body is locked in fight-or-flight.

• The Trap of Trying to "Relate": As a relational leader, your instinct is to bridge the gap with vulnerability and transparency. But in a toxic dynamic, your authentic communication is instantly weaponized against you and labeled as a "hidden agenda" or a "character accusation."

• The Spiral of Self-Doubt: A single, sustained campaign of corporate gaslighting from a peer forces you into a perpetually defensive posture. You begin questioning your baseline worth, your track record, and your capabilities as a leader.

• Existential and Financial Anxiety: The psychological safety is so thoroughly stripped away that it triggers a visceral fear of sudden job loss, forcing you to map out worst-case scenarios for your household despite having a stellar reputation.

When you find yourself in this position, you quickly realize you cannot reason with a peer who views collaboration as a zero-sum game. When their defensiveness escalates, it is usually because your competence threatens them.

Years ago, I didn't know how to handle it. Here is how you do.

🤺 Tactical Strategies to Protect Yourself and Reclaim Your Sanity

1. Shift from Battle to Protection

When a peer targets you, your instinct is to fight back, defend your team, and argue with logic.

Stop. You cannot use logic to change the mind of someone who isn't being logical. Instead, pivot 100% of your energy away from winning the fight. Redirect it entirely toward protecting:

• Your mental health

• Your team

• Your boundaries

2. Leverage Operational Distance (The Cooling-Off Period)

If a relationship has degraded to the point of emotional volatility, look to your leadership to enforce structural distance. A formal "no-contact" or "cooling-off" period on specific work streams isn't a penalty, it's a shield. Use that space to let your nervous system reset, and explicitly refuse to track or consume updates regarding that person during the freeze.

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3. Establish Clear Rules of Engagement

When you must interact in broader group settings, do not wing it. Establish strict, operational guardrails ahead of time. If necessary, route critical feedback through a neutral third party or a shared manager who can act as the sole voice for contentious topics. This keeps the toxic dynamic out of the room and protects the psychological safety of your direct reports.

4. Recognize Projection for What It Is

When a peer accuses you of having a "hidden agenda," being "focused on personal visibility," or "putting the business at risk," look closely at what they are actually doing. More often than not, these highly specific accusations are exact blueprints of their own behavior and anxieties. Recognizing that their vitriol is a reflection of their own internal panic not your performance is crucial to detached survival.

5. Separate the Systemic Friction from Personal Worth

Toxic behavior often thrives in poorly defined organizational structures. When operational support is weak and cross-functional lines are blurry, friction is inevitable. If a peer uses those structural gaps to attack your leadership, remind yourself that the broken system is an operational problem for the company to solve, not a personal deficit for you to internalize.

🔬 Under the Microscope - Executive Fear and Greed

To truly neutralize this toxicity when it is aimed squarely at you, you have to understand the invisible mechanics behind it. This hostility is rarely personal; it is structural, driven by a volatile cocktail of fear, greed, and corporate survival.

At the executive table, wealth accumulation and status act as potent intoxicants capable of reshaping even the most grounded individuals. When a leader's lifestyle inflates in lockstep with their skyrocketing income, the pressure to maintain that momentum ceases to be just a goal; it becomes a relentless, gnawing force. They aren't just managing a department; they are defending their lifestyle.

In the corporate shark tank, you are constantly measured against your peers, and your perceived value is a shifting battleground. When survival hinges entirely on demonstrating unwavering, quantifiable impact, anyone who seems to alter the narrative or challenge the status quo is viewed as an existential threat. Complacency is a death sentence in this environment, and when a peer operates out of the fear of losing their seat, their defense mechanism is to strike first.

Landing a top design leadership role in tech is a huge achievement, but staying there takes hard work and a smart approach to workplace politics. When you find yourself targeted by others, it is often because your actual talent and success threaten their sense of job security.

🧠  The Short of It Is

Acute workplace toxicity is an energy drain designed to make you question your integrity and your value. When you encounter a peer operating out of deep insecurity and hostility, stop trying to fix the relationship. Lean on your leadership to build structural buffers, protect your nervous system at all costs, and remember that their hyper-defensiveness is a direct reflection of how threatened they are by your authentic capability.

That’s all for this week!

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or gift a copy of my book to your team

• Subscribe to, or share this Newsletter with a friend

• Chat with my AI assistant to learn more about how we could work together

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏰ Today in 5 Minutes or Less

You will discover the two hidden systemic traps keeping brilliant design leaders stuck in endless interview cycles, why standard executive positioning fails in the current market, and the exact strategic shift needed to reclaim your corporate authority and land your next high-impact leadership role.

The New Wild West of Tech Leadership

The modern tech landscape has turned into the Wild West for senior design leadership. Waves of corporate restructuring have displaced some of the most seasoned, brilliant product design minds in big tech.

When you have spent a decade or more steering major enterprise platforms, climbing to principal or director levels, and driving cross-functional alignment, you expect the job market to meet you with a certain level of professional maturity. Instead, leaders are encountering an unpredictable, chaotic ecosystem that leaves you feeling completely disconnected from your career path.

Through deep consultations with executive design practitioners navigating this exact transition, two critical, painful patterns have emerged.

Trap #1: The Exhausting Portfolio & Identity Pivot

"I’ve changed my portfolio about 10 times, waffling back and forth. I think it’s just insecurity... I keep repositioning myself, and even my LinkedIn profile, I keep obsessively changing it... because you put all that time and energy into aligning yourself, you get your hopes up, and then it falls through."

When an executive is abruptly separated from a long-term corporate home, an identity crisis almost always follows. In an anxious bid to remain highly employable across a vast range of openings, many leaders fall into the trap of obsessively over-editing their professional footprint.

You spend weeks rewriting summaries, re-arranging case studies, and waffling between positioning yourself as elite Individual Contributors (ICs) who can build complex interactive prototypes, or as strategic directors who manage large budgets and build design orgs.

This constant tactical shape-shifting doesn't make you look more versatile, it dilutes your professional impact. It creates an alignment gap where their tailored resume contradicts their public LinkedIn profile, leaving hiring teams confused about their true zone of genius.

Trap #2: The Recruiter Screening "Ghost Transcript"

"What I’ve learned is if you think it’s just a screening call with the recruiter, it could actually be the interview, because now they’re recording it, sending the notes to the hiring manager, sending the transcript to the hiring manager. A couple times I wasn’t prepared, because I didn’t realize that was the interview... They act like we’re going to be talking a lot, and then they just fall off the face of the earth."

The hiring mechanics in big tech have fundamentally changed. Senior leaders are entering what they assume is a casual, introductory touchpoint with an internal recruiter, only to discover it was a high-stakes gatekeeping exercise.

In the current market, these initial phone or video screenings are routinely recorded, automatically transcribed, and delivered straight to the desks of decision-makers.

When you step into that call casually, failing to treat a non-technical recruiter with the same executive precision you would give a Chief Product Officer, you get trapped. They expect a fluid, human conversation, but instead, you are judged on a cold text transcript, resulting in sudden rejections and unexplained "ghosting" after calls that seemingly went beautifully.

The Executive Insight: Shifting from Charisma to Measurable Impact

Many senior leaders believe they are losing out on roles simply because they aren't the loudest or most performative person in the room. They watch roles go to youthful charismatic candidates and assume they need a total personality makeover.

But after spending 30 years in the tech industry navigating Director, VP-level design and Chief Design Officer leadership roles at companies like Apple, Meta, and Yahoo, I can tell you that long-term corporate authority isn't built entirely on performative charm. It is built on strategic alignment and driving organizational clarity.

Your greatest asset as an executive is your ability to step into highly ambiguous, politically charged, or contentious corporate environments, zoom out, connect disparate platform initiatives, and align cross-functional engineering and product partners toward a clear, profitable path of action that speaks directly to the business bottom line.

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How We Solve This Together

To break out of the interview loop and confidently step into your next senior role, you do not need to make seismic, exhausting career shifts. You are much closer than you think.

Through my foundational Leadership Accelerator Program, we focus on a structured, four-session framework explicitly designed to address these executive friction points:

1. Lock Down Your Definitive Positioning: We stop the cycle of obsessive portfolio editing. We pinpoint your exact leadership pillars and build a cohesive, singular professional narrative across LinkedIn, your resume, and your portfolio so corporate advocates can easily champion you.

2. Build Your Business-Outcome "Source Stories": We reconstruct your career history around quantitative, high-impact business metrics using executive narrative frameworks informed by your leadership strengths. We translate your design investments directly into core metrics that business leaders care about such as increasing lifetime value,  scalability, and reducing churn.

3. Master the Recorded Screening: We build bulletproof frameworks, rehearse Q&A so you can navigate modern recruiter screenings, treating every recorded interaction as an executive panel so your strategic value leaps off the transcript page.

4. Dismantle Limiting Beliefs: We identify and neutralize the internal saboteurs and market anxieties that naturally creep in after a layoff, ensuring you maintain a commanding, unshakeable executive presence in final round panel discussions.

When I was at Meta, Yahoo and Apple, I sat on the other side of the hiring table. I know exactly how executive talent budgets are allocated, how headcount is quietly held or released behind the scenes, and what a hiring committee looks like when a transcript or case study lands on their desk. This framework works because it aligns your presentation directly with the cold realities of executive-level decision-making.

🧠  The Short of It Is

The tech market hasn't run out of brilliant design leaders, it has run out of human oversight. The traditional path of casual networking and hyper-flexible positioning is officially dead. It simply cannot survive today's high-volume, automated corporate screening filters, which were designed to eliminate human bias but ended up eliminating human nuance. When algorithms handle the initial gatekeeping, a flexible narrative is a losing strategy; you need an unshakeable, data-driven positioning statement that leaves zero room for misinterpretation.

To land a director or principal role today, you must treat your own career narrative with the same rigorous, strategic, and data-driven precision you bring to enterprise product design.

If you are a leader tired of navigating the job hunt in circles, let's bring clarity to your unique value proposition.

Book a Discovery call with me today. Let’s map out a bulletproof strategy to reclaim your executive presence, lock down your professional narrative, and fast-track your path back into a leadership role that matches your true strength, passion and expertise.

That’s all for this week!

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to, or share this Newsletter

• Talk to my assistant

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏰ Today in 5 Minutes or Less

Understand the true structural driver behind the latest wave of AI tech layoffs, and discover the counterintuitive strategy of using a career break to attract higher-paying, more fulfilling roles.

The AI Re-Org

The tech industry is currently navigating a massive second wave of workforce reductions. If you’ve been watching the headlines, or worse, if you’ve recently been handed a severance package, it feels incredibly heavy.

According to data from trackers like Layoffs.fyi and SkillSyncer, over 180,000 tech jobs have been cut globally.

But there is a distinct through-line to these cuts that differentiates them from the standard belt-tightening of previous years. This isn’t just about trimming fat; it’s a massive, industry-wide structural shift. Companies are aggressively reducing traditional IT, recruiting, and core software engineering and design roles to free up capital for the "AI arms race", specifically to fund massive data centers, specialized chips, and AI-native operating models.

The Landscape: Where the Cuts Are Happening

To understand the scale of this pivot, we only have to look at how capital is being aggressively reallocated across Big Tech, digital platforms, and hardware frameworks:

• Big Tech & Enterprise Giants: Oracle enacted a massive restructuring to fund its AI cloud infrastructure, cutting up to 30,000 roles globally. Meta cut roughly 8,000 positions while permanently freezing an additional 6,000 open roles to offset a staggering $135 billion in AI capital expenditure. Meanwhile, Dell reduced its headcount by roughly 10% to prioritize its enterprise AI server business, and Cisco slashed positions to pivot toward AI-driven network security.

• Digital & Software Platforms: Intuit announced a 17% global workforce reduction to aggressively hire into AI-product engineering. Wix cut 20% of its workforce to absorb the computing costs of shifting toward AI-assisted "vibe-coding" systems, and Snap Inc. reduced its workforce by 16%, explicitly noting that automation allows smaller teams to handle repetitive work at higher velocity.

• Hardware & Fintech: Block (Square/Cash App) is shrinking its workforce by nearly 40% as Jack Dorsey pivots the fintech infrastructure to an AI-first framework, while Coinbase cut 14% to transition toward an AI-native operational structure.

The "AI Washing" Nuance: Market analysts note a rising trend of AI redundancy washing. While many of these companies are genuinely pivoting to machine learning infrastructure, some firms are using the industry-wide AI narrative as a convenient shield to justify standard cost-cutting to shareholders.

Whether the structural pivot is authentic or a narrative shield, the human cost is identical.

Ian’s Story: From Passion to Exhaustion

Ian has been a creative leader in tech for 20 years, helping companies scale and mature UX organizations. He’s built world-class teams, raised the bar on design quality, and earned deep respect across the industry.

But recently, his work environment became fear-driven and highly political. After laying off half his team, Ian found himself working twice as hard to achieve more with fewer people, all while being asked to "leverage AI" to keep the company competitive. The dysfunctional dynamics and unclear expectations eventually took their toll: Ian burned out, and shortly after, he was laid off.

Two months have passed. This week, signing on to collect unemployment benefits felt like a brutal wake-up call. He told me he felt "weak" for not being more productive in finding his next move. He wanted to get over his funk and land a job. But his tank is empty. He is completely done pushing UX boulders up a hill.

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The Danger of Fear-Based Decisions

If Ian, or you, takes on a new Head of Design or VP role from this place of fear, depletion, and negativity, it almost certainly ends in disappointment.

Taking a leadership role only to pay the bills rarely works out. As leaders, our core values drive our behavior. If your values are misaligned with a hyper-political, cost-cutting business, no amount of technical skill, hard work, or design best practices will prevent you from being marginalized by decisions completely out of your hands.

When we are desperate, we delegate our future to recruiters, headhunters, and job boards. We treat hope as a strategy. But hope is not a strategy.

Ian’s story is incredibly close to my heart because it is my story, too. The third time a tech company riffed a product design organization I had poured my soul into building, my heart broke. 

I knew I couldn't cross another corporate threshold, badged and fingerprinted, running on fumes. I didn't know what was next, and it took a coach to help me find my way through. But before I could figure out the strategy, I had to do something radical: I had to stop and rest. “Like a muddy glass of water, if you let the water settle, the mud will sink to the bottom, and the water will become clear.” Nyoshul Khen Rinpoche

Me Offboarding from Meta in 2018

The 7 Types of Depletion (And How to Fill your Tank)

If you are coming out of a toxic or exhausting corporate environment, standard sleep won't fix it. In her book Sacred Rest, Dr. Saundra Dalton-Smith outlines seven distinct ways we experience depletion. To find your spark again, you need to identify exactly where you are empty:

1. Physical Rest: Allowing the body to recuperate (sleep, naps, gentle stretching).

2. Mental Rest: Giving your mind a break from cognitive processing.

3. Sensory Rest: Disconnecting from the sensory overload of screens.

4. Creative Rest: Turning off the problem-solving brain. Stepping away from trying to "solve design" and instead allowing yourself to experience beauty without needing to critique it.

5. Emotional Rest: Having the space to freely express your authentic feelings without performing. This means dropping the "polished tech leader" mask and speaking honestly with a therapist, coach, or trusted peer.

6. Social Rest: Differentiating between relationships that revive us and those that exhaust us, and choosing to spend time only with positive, grounding people.

7. Spiritual Rest: Reconnecting with a deep sense of belonging, purpose, and core values outside of your job title.

The Strategic Leap: The Power of an Intentional Career Break

When a layoff happens, our immediate survival reflex is to run toward the next burning building. But there is an immense, counterintuitive power in choosing a formal career break instead.

I have taken two significant career breaks in my life. On both occasions, the choice felt terrifying. My inner critic screamed that I was falling behind, that my network would forget me, and that my value was plummeting.

The exact opposite happened.

By taking the time to fully rest, clear the mud from the water, and realign with my baseline values, I entered the market as a completely different caliber of candidate. I wasn't interviewing as a burned-out, cynical leader looking for a safe harbor; I was interviewing as a re-energized, strategic visionary who knew exactly what she brought to the table.

Because of those breaks, I attracted significantly higher-paying and deeply interesting work.

A career break isn't a gap on your CV; it’s an investment strategy. It gives you the space to ask: Who am I when I'm not pushing this boulder?

If you are sitting in the mud right now, give it time to settle. Don't rush into deciding with a cloudy mind. As the master Nyoshul Khen Rinpoche beautifully wrote:

 Rest in Natural Great Peace

This exhausted mind,

Beaten helplessly by karma and neurotic thoughts

Like the relentless fury of the pounding waves

In the infinite ocean of samsara.

Rest in natural great peace.

🧠  The Short of It Is

Take a breath. Step away from the screen. Let the mud settle. Your next chapter depends on the clarity you find right here.

The current wave of tech layoffs isn't just standard belt-tightening; it is an aggressive, industry-wide structural reallocation of capital toward AI infrastructure. If you have been caught in this transition and find yourself exhausted, jumping straight into the next available leadership role out of fear is a recipe for misalignment and further burnout.

Recognize that true recovery requires addressing your specific depletion across the 7 types of rest. Choosing an intentional career break isn't a setback, it is a high-ROI career strategy that allows the mud to settle, gives you your spark back, and ultimately positions you to command higher pay and far more rewarding work on the other side.

That’s all for this week!

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to, or share this Newsletter

Photo attribution: Jonathan Castañeda, “A man lying on the side of a road”

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏰ Today in 5 Minutes or Less

You’ll learn the exact frameworks four design executives used to stop defending "design craft," master the art of safe pushback in high-pressure rooms, and turn a chaotic onboarding transition into long-term organizational power.

🏆 The Reality of the Executive Transition

When you step into a new executive role at a tech company, you aren’t just inheriting a product roadmap; you are inheriting legacy decisions, political undercurrents, and shifting C-suite dynamics. 

To demonstrate exactly how executive coaching helps design leaders survive and thrive through these high-stakes transitions, let’s look at real moments from four different leaders navigating high-pressure corporate environments. Here is how tailored coaching turns a chaotic onboarding experience into a masterclass in strategic leadership.

1. Shifting from "Design Craft" to "Executive Speak"

🔴 The Issue: Bob stepped into a high growth environment driven by a highly charismatic, visionary CEO with a hard nosed finance background. His immediate challenge was a relentless torrent of subjective, emotional feedback coming from public forums and customer reviews. The C suite treated this qualitative noise as an absolute source of truth, causing executive panic and reactive demands: "Fix it now! Launch a feature!"

The Internal Toll: Bob knew the core user experience was cluttered, but he felt trapped trying to break down a mountain of "tiny experiential cuts" (accessibility, legibility, disjointed features) into traditional design metrics that the data-starved executive team simply ignored.

🟠 The Coaching Shift: We pushed Bob to look past the craft of design and frame the problem entirely in the financial language his CEO and board actually care about:

• Reframe Clutter as Cost: Clutter isn't an aesthetic issue; it is a retention killer. We reframed the messy user experience as a metric the C-suite tracks: increased churn and reduced speed-to-value.

• The Power of Proxy Data: Bob mapped out how he could tie design hypotheses directly to protecting the critical 60-day revenue window, transforming a subjective critique into a business-critical revenue defense strategy.

🟢 The Outcome: Without a coach, Bob would likely have spent weeks creating elaborate user experience teardowns, only to watch them get dismissed by a board that doesn't understand digital product cycles. Instead, he immediately pivoted his communication strategy, stepping into the next executive meeting speaking the language of ARR, churn mitigation, and customer lifetime value, instantly boosting his credibility.

2. Mastering the "Safe Pushback" in High-Pressure Rooms

🔴 The Issue: In a previous leadership role, Joane had been dinged for pushing back against executive decisions, with colleagues labeling her as "not a team player." Now, entering a highly reactive corporate culture where action was frequently confused with progress, she was surrounded by chaotic, unvetted feature requests.

The Internal Toll: She felt a profound anxiety around confrontation. She noticed a dangerous blind spot: she was absorbing the room's anxiety, staying silent, and running the risk of letting her design team get crushed by reactive work.

🟠 The Coaching Shift: We staged a real-time roleplay to practice a bulletproof executive toolkit: the power of 7-to-10-word "How" and "What" questions. Instead of taking a defensive posture or saying "we can't build that," Joane practiced putting the strategic weight right back onto the room using clinical curiosity:

• “What impact do we believe this specific user feedback is having on retention?”

• “What do we think about this request in relation to the other priorities we see?”

• “How are we going to measure the success of this fix against our current benchmark?”

🟢 The Outcome: Without a coach, Joane would likely have defaulted to silence to stay "safe," allowing her lean team to become an execution sweatshop for executive whims. Instead, she broke a legacy limiting belief in real time, gaining a tactical framework to assert her authority without ever being perceived as defensive.

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3. Turning Political Chaos into Structural Power

🔴 The Issue: John inherited a massive operational mess. Before he arrived, a third-party agency had abruptly relaunched the core product without any isolated testing, cutting out features users loved and dropping conversion rates by half. Rogue internal tools and fragmented agency projects were still landing on John’s plate simply because "an executive asked for it."

The Internal Toll: John found himself entirely reactive, exhausted from trying to pull back the tentacles of a broken vendor contract while managing a severe resourcing deficit.

🟠 The Coaching Shift: We identified that John didn't just have a design problem, she had a systemic corporate governance problem. We reframed this chaos as his single greatest opportunity to establish long-term organizational influence:

• Own the Operating Procedures: The leaders who hold true power are those who own the standard operating procedures. We coached John to partner directly with his boss to co-create a strict prioritization gatekeeper system.

• Deploy Cross-Functional Alliances: We designed a strategy where John approached the cross-functional insights and marketing leads to create a shared "leaderboard" tool. This intercepted subjective feedback before it hit the executive level, filtering it through a co-owned feasibility and financial-impact scoring model.

🟢 The Outcome: Without a coach, John would have remained isolated in his silo, fighting off ad-hoc requests one by one. Instead, he stepped into a proactive, company-wide leadership role, using relationship building to align the C-suite around an operating model that permanently protects his team's focus.

4. Navigating the Legacy Leader Transition

🔴 The Issue: Liz stepped into a massive executive role inheriting a highly established team that had been built entirely from the ground up by a beloved, departing leader. To complicate matters, the former leader was staying on for a multi-week transition period, and the domain itself was a highly technical "black box" that Liz needed to master quickly.

The Internal Toll: Liz’s natural instinct as a high achiever was to immediately shift into "doing mode", planning tactical role shifts and trying to structurally manage the transition plan before building trust. She felt immense pressure to establish strategic credibility instantly while navigating the awkwardness of not stepping on her predecessor's toes.

🟠 The Coaching Shift: We shifted Liz from "doing mode" to "being mode," recognizing that the initial transition phase was entirely about human rapport:

• Lead with Empathy: We coached Liz to pause the tactical planning and make her initial interactions about understanding the departing leader's legacy and concerns, building deep trust right away.

• Accept the Umbrella: We looked at how to let the departing leader hold up their "parental umbrella" over the organization for the time being, freeing Liz from worrying about winning over the entire massive department all at once.

• A Ground-Up Networking Strategy: Instead of trying to manage the whole organization instantly, we deployed a targeted, 1-on-1 organic connection strategy, asking a simple question to key stakeholders: “Who else is someone I need to get to know?”

🟢 The Outcome: Without a coach, Liz likely would have entered as an aggressive disruptor, triggering widespread uncertainty and defensive behavior from the legacy team. Instead, she was able to step back, protect her energy, and design a transition framework rooted in empathy, entering the organization as a relationship-driven executive ready to accelerate the business.

🎭 The Hero's Journey: Why Walk It Alone?

Bob, Joane, John, and Liz are the ultimate heroes of these stories. They didn't choose comfortable, stagnant organizations; they deliberately chose complex, high-stakes puzzles because that is where elite design leaders grow. But navigating these ambiguous corporate waters can frequently make even veteran executives feel "out of their element."

An executive coach doesn't do the work for you. A coach acts as your objective sounding board, your political navigation system, and your partner in turning organizational friction into professional leverage.

Are you stepping into a new executive design role or attempting to steady a product organization experiencing turbulence? 

🧠 The Short Of It Is 

Stepping into an executive design role isn't a test of your craft, it’s a test of your political navigation and business translation skills. You don't have to figure out the unwritten rules of the C-suite by trial and error. A coach provides the objective framework to protect your team, scale your influence, and secure your seat at the table from day one.

Let’s ensure your onboarding phase is smooth, highly visible, and strategically bulletproof.

Book a Strategy Breakthrough Session With Me Today

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to, or share this Newsletter

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏰ Today in 5 Minutes or Less

The corporate narrative would have you believe that a PIP is a merit-based intervention designed to help an underperforming employee close a professional gap. But those of us who spent have time working  in tech environments know the truth. A PIP is rarely about performance. It is a highly mechanized compliance process used to manage headcount, flatten organizations, or push out individuals who no longer fit a rapidly changing corporate puzzle.

It happens to the best of us.

The Anatomy of a Setup: A Step-by-Step Story

I recently worked with a high-caliber leader, a brilliant, six-year veteran at a tech company with a deep track record of high-level accomplishments. They weren't an under performer; they were a casualty of organizational flattening.

When we looked back at how this nightmare came to be, it unfolded in a calculated, step-by-step sequence:

• Step 1: The Disruption of the Safe Harbor. Initially, this leader’s team had full autonomy to build an ambitious, visionary product roadmap. They had formed an incredibly tight, trusted working relationship with a supportive manager who championed their growth.

• Step 2: The Structural Floor is Cut Away. The corporate flattening machine arrived. The supportive manager was promoted out of the org, adjacent teams suddenly merged, and a new manager stepped in. In an instant, the exciting, strategic projects they were hired to lead vanished.

• Step 3: Smeared with Corporate Ambiguity. They were suddenly dropped into a tense political environment. When the leader raised strategic concerns about features never launching, their feedback fell on deaf ears. Management began using corporate ambiguity as a weapon to keep them in limbo.

• Step 4: The Invisible Goalposts. They were sending daily updates meticulously documenting their accomplishments and architectural blockers, only to be met with vague managerial deflections devoid of actual feedback.

• Step 5: The Impossible Timeline. Despite earning a "meets high" performance rating only weeks earlier, they were given an unrealistic checklist. It required securing cross-functional project approvals within a strict eight-week deadline, a task made impossible by the organization's flat structure and heavy red tape. The trap was set: it was a Performance Improvement Plan (PIP) in all but name.

The Silent Psychological Toll

This is where the corporate machinery does its most insidious damage: it attacks your sanity. When you are operating in a rigged system where your attempts to solve problems are ignored, you experience profound psychological erosion.

This leader shared that they were caught on a grueling emotional roller coaster, struggling to sleep and feeling their mind constantly drifting. Their internal battery plummeted to just 10%. Waking up, trying to stay grounded, and logging on felt like an insurmountable weight.

When an elite performer is subjected to gaslighting metrics, they begin to exhibit classic survival instincts. In this leader's case, their survival saboteurs took the wheel. They began shutting down and turning off completely, treading water professionally just to stay alive emotionally. The corporate machine takes individuals with immense professional confidence and grinds them down until they are paranoid, exhausted, and wondering if they are losing their minds.

The US-Centric Playbook Trap

The legal and operational options provided in these high-stress moments are violently US-centric. Tell me if I’m wrong here?

In the United States, the HR playbook is heavily structured around American labor dynamics. Employees are taught that they have three levers: try to survive the impossible checklist, negotiate a severance package to walk away, or leverage federal protections like the Family and Medical Leave Act (FMLA) or short-term disability benefits (often paying 60% of base salary for 12 weeks) to buy time and preserve their mental health.

But tech giants are constantly changing the rules under the hood. As this leader discovered after consulting with specialized legal counsel, companies have quietly shifted policies so that taking a medical leave of absence no longer pauses or erases a review window; it simply waits for you on the other side. This turns a period meant for medical recovery into an added layer of hyper-anxiety and paranoia. For international tech workers or those operating under completely different regional labor laws, navigating a system designed strictly around American corporate compliance feels like trying to speak an alien language without an alphabet.

When Your Face No Longer Fits: My Story

I validate every ounce of the roller coaster this leader rode, because I lived it.

In 2018, I found myself sitting in an HR room at Meta (then Facebook). I had 25 years of corporate execution under my belt. Yet, corporate rooms can be incredibly unyielding to the messy realities of being human. At the time, I was dealing with the sudden, severe onset of menopausal symptoms: debilitating anxiety, brain fog, overheating, joint pain, chronic insomnia, unexplained tearfulness, anger, and sheer physical exhaustion. It made me feel entirely "unfit for purpose" in an environment that demanded 24/7 hyper-performance.

Corporate policy didn't have a placeholder for my biology. Because I kept my symptoms to myself, management only saw the decline in my performance, which ultimately led to a PIP. Back then, I had no idea that a sudden drop in estrogen could be so debilitating, or that it could derail my career. The ultimate self sabotage.

Leaving Meta was the inflection point of my career, and ultimately, my greatest blessing. It was the catalyst that forced me to step off the corporate treadmill, embrace entrepreneurship, and build my own business as an executive coach. I turned a dark, mechanized corporate exit into a massive personal victory.

I am writing this eight years later, triggered by last week’s announcement of 8,000 Meta employees being laid off. The news brought it all flooding back, prompting me to write about an experience that, at the time, felt far too shameful and taboo to ever disclose.

Putting this into words now is part of my own healing process, and I am grateful to you for reading this far.

My intention here isn't to cast blame or harbor bitterness. It is simply to acknowledge a fundamental truth: the body keeps score. Performance Improvement Plans (PIPs), whether you are the one receiving them or the leader being forced to hand them out, have deep, far-reaching consequences. They leave an imprint that ripples out for years, bringing both good and bad transformations long after the corporate doors have closed.

The Strategic Blueprint: Reclaiming Your Power

If you are currently sitting in the shadow of a PIP, or watching your organization flatten around you, you are likely feeling completely powerless. Here is the exact, detailed framework to help you handle this situation, preserve your sanity, and take a little of the power back from the institution:

1. Stop Performing for a Rigged System

When a PIP is compiled with metrics that are mathematically or cross-functional impossible to achieve, stop destroying your physical and mental health trying to jump through their hoops. Take the corporate checklists with a massive grain of salt and stop taking them personally. I know, this is much easier said than done.

Shift your mindset: make them do the operational and administrative work. Let them run around trying to document their boxes while you quietly disconnect your identity from their game and protect your precious energy.

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2. Execute Self-Preservation Logistics

Do not wait for an abrupt structural change to catch you off guard. Assume you could lose access to your corporate accounts at any moment and quietly map out your exit infrastructure:

• Shelve Your Work: Ensure your key case studies and design files are safely cataloged.

• Record Your Impact: Capture video walkthroughs of your prototypes and interactive models so you aren't forced to rebuild them outside of the company's ecosystem later.

• Pull Business Metrics: Carefully gather all your historical impact data and business metrics while you still have internal server access to build an ironclad external portfolio.

• Secure Your Directory: Build a private list of names, personal emails, and LinkedIn profiles for every trusted ally, cross-functional peer, and reference-ready colleague.

• Read my newsletter on Design Career Insurance for tips on what to do before you turn in your badge.

3. Time-Box the Problem and Explore Mutual Separation

It is structurally impossible to effectively look for your next step while a corporate guillotine is hanging over your head. Decide on a fixed timeline. Rather than executing a blind leave of absence that leaves the problem looming over you, consider opening a direct conversation to negotiate a mutual split. Walk into the room with clear terms: define a clean professional handoff, negotiate an exit date that protects your unvested equity schedules, demand a payout for accrued holiday time, and request structural coverage for career transition tools like coaching. Get paid to walk away on your own terms.

4. Reclaim Your Network and Intellectual Capital

Your world-class track record, your industry accomplishments, and your professional dignity do not vanish the day an HR representative opens a case file. Reclaiming control means activating your network externally and not withdrawing from circulation. Dedicate your energy to micro-outreach: pick three people a day, former trusted colleagues, industry friends, or professionals who have successfully transitioned into new roles. Don't ask them for a job; simply initiate open-ended, 15-minute coffee chats to share what you are building and discover what they are seeing in the broader market.

A PIP feels like a sudden, catastrophic end to a career. In reality, it is almost always just the universe violently shaking you out of a corporate room that you have entirely outgrown.

To your next chapter

That’s it for this week.

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to, or share this Newsletter

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏰ Today in 5 Minutes or Less

Learn how to transition from a highly-compensated individual contributor to an influential executive by mastering the art of ally-building and strategic sponsorship.

🤑 High Income, Low Influence: The Reality of the Invisible Ceiling

Many creative leaders reach a point in their career where the ladder seems to stop, despite their immense talent. They find themselves at prestigious, stable companies, earning a high income, yet feeling "under-leveled" and excluded from the "inner circle" where the most meaningful work is defined.

The problem often isn't a lack of skill; it's a structural and cultural gridlock. In many established organizations, leadership turnover is nearly non-existent, and the hierarchy is so rigid that it feels like "swimming in the ocean" without a shore in sight. These leaders often feel they are moving horizontally rather than upward, trapped by an insular culture that values tenure over fresh perspective.

😲 The Real Cost: Stagnation, FOMO, and Fading Relevance

Stagnation isn't just about a missing title; it’s an emotional tax that grows every day. When you are stuck in a "cautious and deliberate" environment while the rest of the industry is sprinting toward a new technological frontier, the "Fear Of Missing Out" (FOMO) becomes a heavy weight.

One leader recently shared that despite having a "good job" at a tech company, they felt like they were wasting their potential. They watched faster-moving startups become the new "industry darlings," feeling as though their best years were being spent building internal tools or "raising the bar" on things that aren't transferable to the outside world. The emotional toll is significant:

• The "One Step Forward, Two Steps Back" Feeling: The frustration of having great conversations with VPs, only to feel you are still "touchable" and vulnerable because you lack a true protector or sponsor.

• The Fear of the "Empty Story": The deep-seated worry that after three years, you’ll look back and realize you have nothing concrete to show for your time, no products launched, just horizontal moves.

• Isolation: Feeling like an outsider looking into a "clicky" inner circle that doesn't seem to have a seat for you, regardless of your expertise.

🪤 The Trap of the "Subject Matter Expert"

The most common mistake is continuing to act as a Subject Matter Expert, the person who does the work and pushes their own ideas. While technical excellence got you here, it won't get you there. To break through, you must shift your focus from the doing of the work to the being of a leader. At this stage, career growth is no longer about having the best ideas; it is about:

Influencing without Authority:Leading projects and teams even when you don't have direct reporting lines. 

• The Tip: Find the "What’s In It For Them" (WIIFT). Since you can't mandate action, align your project's goals with the personal or professional incentives of the people you need. When you help them win, they will naturally want to help you lead.

Strategic Communication: Moving away from technical jargon to high-level clarity and brevity that resonates with executives. 

• The Tip: Start with the headline, then bottom-line it. Use the BLUF method (Bottom Line Up Front). Executives care about outcomes, risks, and resource needs, not the technical weeds. Give the conclusion first, and only dive into data if they ask.

Building Allies, Not Just Networks: Shifting from "positioning yourself" to genuinely learning the perspectives of others to build a foundation of support.

• The Tip:Practice operational empathy. Instead of pitching what you do, ask others about their biggest bottlenecks and priorities. By understanding their world and offering small wins to help them solve their problems first, you build bulletproof, reciprocal trust.

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💉 How You Move the Needle

When you’re caught in organizational gridlock, trying harder isn’t the answer, trying differently is. This is my coaching  roadmap to help you break the stagnation, align your worth, and reclaim your leadership edge.

Step 1: Time-Box Your Goals

We define time-bound milestones for your career trajectory. This ensures every project you take on remains deeply meaningful and drives you forward, whether that’s within your current company or positioning you for your next big leap.

• The Impact: Eliminates drift. You stop reacting to daily fires and start executing a proactive strategy that keeps your career trajectory pointed upward.

Step 2: Audit and Align Your Leadership Integrity

We identify exactly where you are over-indexing (wasting energy) or where your current day-to-day role is out of alignment with who you’ve become. We then close the gap between where you are today and the highest expression of your potential.

• The Impact: Unlocks magnetic authority. Coming into alignment with your authentic leadership skills changes how you command a room. It naturally attracts leaders who respect your values, support your growth, and are ready to compensate you for what you are truly worth.

Step 3: Architect a Stakeholder Communication Strategy

We conduct a 360-degree review of the internal and external centers of influence, the people whose opinions hold power over your career today. Using my communication plan, you will track and manage these relationships like a high-value pipeline.

• The Impact: Cuts through the noise. You stop trying to please everyone. Instead, you focus 100% of your energy on the most qualified, influential relationships that drive real organizational outcomes, while confidently ignoring the rest.

🚀 The Short of It Is

By aligning your internal leadership value and strategically managing your external network, you dissolve the gridlock holding you back and step back into your full professional power. Ready to Break Through your Current Plateau? If you feel like you’re doing the work but stuck, let’s talk. I invite you to book a free 45 minute strategy session with me to map out your path from expert to executive. Book a Strategy Call with Me

That’s it for this week.

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to this Newsletter

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

The "Bob" Problem 👀

I was coaching a Design Director this week—let’s call him Bob. He’s brilliant, his team is elite, and their work is impeccable. Yet, he was feeling a very modern kind of anxiety.

In the current "economic efficiency" climate, Bob felt his department's value was being sidelined. He told me:

"I feel like there’s a silent code in the office: Product and Engineering own the 'Why' and the 'What,' and my team is just here to make the AI look good."

If you feel like your department is the first on the chopping block, it’s usually a translation error. You are speaking the language of "User Delight," while the CFO is speaking the language of "Business Impact."

📐 The Angle: The Business of Design

Coming from my time at Apple and Meta, I saw that the most successful leaders don't try to prove that a specific hex code increased the stock price. That’s a losing battle. Instead, they use Behavioral Proxies. A behavioral proxy is a "clue"—a specific, countable action that tells you something big is about to happen before it shows up in the bank account.

☕ The Coffee Shop Analogy:

Imagine you own a coffee shop. You want to know if people love your brand.

• The Fluff: A customer says, "I love this place!" (Nice, but unquantifiable).

• The Proxy: The customer brought a friend. If you see more people bringing friends, you can be 90% sure your sales will be up next month.

Lagging vs. Leading: The Boardroom Gap

Most businesses track Lagging Indicators (total profit, yearly revenue). The problem? By the time you see those numbers, you can’t change them.

Smart leaders track Leading Indicators (Behavioral Proxies)—actions customers take right now that predict future money.

🏆 How Bob Used This to Win

Bob realized he couldn't just say a "cleaner layout" made the company £1 million. He had to connect Pixels to NRR (Net Revenue Retention). To make his case, Bob’s chosen behavior (Feature Adoption Depth) had to meet three criteria:

1. Observable: He can see in the data exactly who is clicking the AI tools.

2. Correlated: Users who try 3+ features almost never cancel. There is a direct link between "usage" and "staying."

3. Influencable: Bob’s team can’t force a customer to pay, but they can make those features easier to find and faster to use. Design owns the influence.

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The Transformation: "Fixer" vs. "Strategic Leader"

The Old Way (The "Fixer" Voice):

"We’re redesigning the dashboard to make it look modern and reduce friction."

• What the Board hears: "We’re spending money on decorations."

🆕 The New Way (The "Leader" Voice):

"Our data shows users who adopt three AI features are 60% less likely to churn. We are redesigning the interface specifically to increase Feature Adoption Depth to protect our NRR."

• What the Board hears: "Bob is a genius who is securing our revenue."

🚀 The Short of It

Executive sponsorship isn’t a gift; it’s the ROI of proving you understand the business. The moment you stop being the person who "fixes the colors" and become the one who "de-risks the roadmap," everything changes. When you own the behavior, you own the "Why."

Ready to bridge the gap?

If you’re struggling to convert your team's design craft into business terms the Board respects, I can help. I have two 1:1 coaching spots opening this month for leaders ready to level up.

Book a Strategy Call with Me

That’s it for this week.

PS: Would you like to receive more leadership strategies? Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to this Newsletter

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏱️ Today in 5 Minutes or Less

You’ll learn how to clear the five mental hurdles that stop us from negotiating, why big tech’s current profits give you more power than you think, and a simple trick to view your contract as a "bug" that just needs fixing.

The Story of "Sarah"

This week's LinkedIn post touched a nerve: the idea that negotiation isn’t a "personality trait" you’re born with, but a skill set you build. I wanted to dive a bit deeper today into the "internal ghosts" that keep us from asking for what we’re worth.

The offer came in, but it was lower than she expected.

My client, we’ll call her Sarah, is a powerhouse Director of Product. She’s led teams through high-stakes pivots and launched Tier-1 features. She has the absolute respect of every engineer she’s ever worked with.

But when that PDF landed in her inbox, she froze. Her internal dialogue took over:

• "The market is tough; maybe I should just take it."

• "If I ask for more, will they think I’m 'difficult' before I even start?"

• "I don’t have a competing offer to use as a hammer."

Fear was in the driver’s seat. Leverage was in the trunk.

Negotiating a job offer is as much a psychological game as a financial one. Most leaders leave money on the table not because they lack the skills, but because they are fighting limiting beliefs. Let’s bust the most common ones:

1. "If I negotiate, they might rescind the offer."

• The Reality: Rescinding is incredibly rare. By the time a company sends an offer, especially a giant like Apple, they have already decided you are the solution to their problem.

I remember this fear well. When I was offered an internship at Apple, the thought of questioning them didn't even cross my mind. They were moving me from a shared flat above a butcher's shop on West Hendon Broadway in London, to Cupertino, California, on a $37k salary. Compared to my $3k student grant, it felt like I’d won the lottery.

Because I was so afraid that "questioning" the offer would make it disappear, I stayed silent. I didn't account for the "bugs" in the move: the extreme cost of California housing, the necessity of a car, and the bite of medical insurance.

I got 1,000% more sunshine, but my actual quality of life was lower than my "shoestring" student budget back in London at the Royal College of Art. Had I treated the offer as a business discussion rather than a gift from the gods, I would have realized that $37k wasn't a windfall, it was a logistical error that needed "debugging."

• The Reframe: Negotiation isn’t an insult; it’s a feasibility study.

2. "I should just be grateful to have an offer in this market."

• The Reality: Your market value isn't dictated by the "vibes" of the economy; it’s dictated by the problem you are solving for this company. Gratitude and fair exchange are not in conflict.

That is, of course, easier said than done when you look at this year's layoff figures. According to TrueUp, so far in 2026,in the US, there have been 273 tech layoffs with 121,111 people impacted (961 people per day). In the UK, Big Tech slashed 80,000 jobs in early 2026, according to Tech Times.

The reasons for these cuts are twofold: an AI Pivot, where companies hire for AI while cutting other roles, and white-collar vulnerability, where middle management and entry-level roles are disproportionately affected.

However, this downsizing or ‘re-structuring” doesn't mean tech companies aren't doing well. Look at the Q1 2026 earnings:

• Alphabet (Google): $109.9 billion in revenue with a massive 81% surge in profits.

• Amazon: $181.5 billion in net sales, up 17% year-over-year.

• Microsoft: $82.89 billion in revenue, marking 18% growth.

• Meta Platforms: $56.31 billion in revenue (a 33% increase).

• Apple: Revenue up 16%, driven by record iPhone demand and services.

Even in the middle of a technology revolution, if you are given a low-ball offer, you need to stand up for yourself because they have the money.

• The Reframe: "I am grateful for the offer, and I want to ensure my compensation reflects the impact I’m going to have on this team."

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3. "They gave me their 'Best Offer' upfront."

• The Reality: Recruiters often have a range. Even if the base salary is capped, there is almost always "wiggle room" in sign-on bonuses, equity, or remote flexibility.

I remember being told an offer was 'final' because of 'internal equity’. The idea that they couldn't pay me more than the current team. I didn't argue; I just asked my future manager if the current budget accounted for the specific expertise I was bringing. 

Two days later, a 'newly approved' retention bonus appeared in the contract. The recruiter wasn't lying about their limit, but the hiring manager found a different pot of money once they realized the cost of not hiring me was higher. Has this ever happened to you?

• The Reframe: The "best offer" is usually just the best offer so far.

4. "I don't have a competing offer, so I have no leverage."

• The Reality: Your greatest leverage isn't another company, it's your unique value and your willingness to walk away. If you say no, the hiring manager has to start an expensive, months-long search all over again.

Many professionals believe they need a "poker chip" in the form of a competing offer to win. I’ve never gone after roles just to get multiple offers, it's just not my style.

It took me until my 40s to finally say "no" to an offer that didn't meet my expectations. When I stood my ground, the pushback was immediate. They suggested there would be "significant risk" in having to go back to the CEO for a higher salary. It was a classic pressure tactic designed to make me fold. I didn't fold. I stayed firm, they got the confirmation, and I got the increase. The delight I felt wasn't just about the extra money; it was the realization that I held the cards all along.

• The Reframe: Your leverage is your data and your specific expertise.

Get Your Copy on Amazon

5. "I'm not a 'Sales Person'; I'm not good at this."

• The Reality: In tech, negotiation isn't "haggling." It’s collaborative problem-solving.

I once accepted a "dream role" that, upon closer inspection, was structurally unsound. The contract was riddled with red flags: an inaccurate title, a lower job level than discussed, and a stifling non-compete clause.

My gut screamed at me to negotiate, but my circumstances shouted louder. I was early in my career and only days away from visa expiration after being let go by Apple when they closed the R&D lab after Steve Jobs returned to lead again in 1997. To avoid the discomfort of confrontation, and the looming threat of deportation, I stayed silent and signed.

The immediate result was that I saved my legal status, but I couldn't save the job. Because the foundation was built on "bugs" I never addressed, the role never truly fit, and I was let go only a year later. 

In trying to protect my future, I realized I had sabotaged my own professional architecture; by not walking away, or at least speaking up, I traded long-term career alignment for a short-term safety net that eventually collapsed anyway.

• The Reframe: Treat it as a technical requirement. You are simply debugging the contract until it functions correctly for both parties.

Back to Sarah

When Sarah and I hopped on our coaching call, she was ready to settle for "good enough." In 60 minutes, we shifted her perspective:

• We separated "Base" from "Package": The recruiter said the salary was at the ceiling. Fine. We ignored the ceiling and looked at the floor: the sign-on bonus and the vesting schedule.

• We scripted the "Neutral Voice": We practiced her ask until the "umms" and "sorrys" disappeared. She stopped sounding like she was asking for a favor and started sounding like a consultant closing a deal.

• The "Preferred Candidate" Pivot: I reminded her: This company isn't doing you a favor. They have a problem, and you are the solution they want.

• The Result: Sarah secured a $15k sign-on bonus, a written path to VP, and a specialized development budget the recruiter "didn't think existed." Most importantly, she started Day 1 feeling fully backed and respected, not "haggled down."

🚀 The Short of It Is

Negotiation is the final stage of the interview. By advocating for yourself, you are demonstrating the very skills they are hiring you for: communication, strategy, and the ability to handle high-stakes situations.

This is one of the four pillars of my 90 Day Career Accelerator program. If you’re expecting an offer soon and want to ensure you aren’t leaving your future on the table, let’s talk. 

That’s it for this week.

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

Hello and welcome to Leading by Design! If you’re new here, add your email to ensure that you receive my next piece in your inbox.

⏱️ Today in 5 Minutes or Less

You will learn how to translate your team’s design output into the high-stakes financial language used by Big Tech executives to secure more influence and resources.

And Then It Hit Me …

I vividly remember my first board meeting. I was immediately struck by how effortlessly everyone around the table grasped the financial data. As the quarterly reports were passed around, all eyes—and plenty of bespoke eyewear—were fixed on those spreadsheets. It was incredible; they could spot a trend or pivot a strategy in seconds.

I watched in awe, and the only thing I could compare it to was the way we experience a design review. You know that feeling when you look at a spec and can instantly see exactly what’s working and what isn't? That was them, but with numbers.

But since Big Tech is where I feel most at home, I’ve put together this "cheat sheet" to help you skip the awkward learning curve. Think of it as your translation guide to the five metrics Big Tech cares about most in 2026 and exactly how your design work makes them move. And hey, if this all seems like old news to you, well done! You're already ahead of the curve.

Top 5 Big Tech Business Metrics and How To Design For Impact

In the world of "Big Tech", where companies like Apple, Microsoft, Amazon, Alphabet (Google), and Meta operate, the five most critical business metrics Big Tech cares about, the strategic "why" behind them and how you can connect, the design impact and how to pitch it for maximum business impact. 

💓 1. DAU/MAU (The Heartbeat Metric)

• What it is: The number of daily and monthly active unique users interacting with a product.

• Why it matters: It measures "stickiness." In Big Tech, attention is the scarcest resource. If this slips, it signals that a competitor (like a new AI agent or social platform) is stealing the user’s most valuable resource: attention.

• Design Connection: If users find a product confusing or slow, they don't return. High DAU/MAU is the result of a frictionless onboarding experience and a clear value proposition that solves a recurring problem.

• The Pitch: “By redesigning the 'Time to First Value' (TTFV), we reduced initial friction, leading to a 15% increase in DAU. Our design ensures the product isn't just used once, but becomes a daily utility."

🥡 2. CAPEX on AI Infrastructure (The Size of the Sandbox)

• What it is: Capital Expenditure is the billions of dollars spent on physical assets, specifically GPU clusters, data centers, and custom silicon (like Google’s TPUs or Amazon’s Trainium).

• Why it matters: It is a proxy for "future-proofing." Investors want to know who will own the compute layer.

• Design Connection: Creating low-latency, "magical" interactions that justify the massive backend costs. All that hardware spending means nothing if the interface is clunky. Design leaders bridge the gap by creating low-latency interactions and generative UI that make the massive compute power feel "smart" and intuitive rather than overwhelming.

• The Pitch: "We are designing the interaction layer for our new AI models. Our goal is to translate our infrastructure investment into 'anticipatory design,' where the system predicts user needs, justifying the high cost of the compute."

🥅 3. NRR (The Ecosystem Trust Score)

• What it is: Net Revenue Retention (NRR), is the percentage of revenue retained from existing customers (including upsells).

• Why it matters: An NRR over 100% means the company is growing even if they don't sign a single new customer. For Amazon (AWS), high NRR proves that once a company starts using their cloud, they inevitably "expand" by adding more services like AI model hosting or database storage. It proves the ecosystem's gravity.

• Design Connection: NRR grows when users find more reasons to stay within your ecosystem. This is driven by cross-product consistency and discovery design. If a user of App A finds App B easy to use because of a shared design language, they are more likely to adopt it. The design connection is in building consistent design systems that make adopting a second or third product feel effortless.

• The Pitch: "By creating a unified design system across our cloud suite, we lowered the cognitive load for existing users to adopt new modules, directly supporting our 120% NRR goal by making 'upselling' feel like a natural feature expansion."

🏆 4. ARPU (The Perceived Quality Bar)

• What it is: Average Revenue Per User (ARPU),  is the total revenue divided by total users.

• Why it matters: It tells the story of how well a company "monetizes the relationship." For companies like Apple, it is the "Services" story. If iPhone sales plateau, Apple must increase ARPU through iCloud, Apple TV+, and App Store fees. A rising ARPU tells Wall Street that the company isn't just a hardware manufacturer; it’s a digital landlord.

• Design Connection: Premium craft and emotional design that makes "Pro" tiers feel worth the cost. ARPU increases when users believe a service is worth paying for (or paying more for). This is the result of high-quality craft and emotional design. It’s the difference between a free tool and a "Pro" experience that feels worth the subscription.

• The Pitch: "We redesigned the 'Pro' tier to focus on exclusive high-value workflows, increasing the perceived value and successfully moving free users to paid tiers, driving ARPU."

Chapter 6. Quantifying Product Design: Key Metrics for UX Design Executives

💕 5. CAC vs. LTV (The Relationship Health Ratio)

• What it is: The cost to acquire a customer (CAC) vs. the profit they generate over time. Long Term Customer Value (LTV).

• Why it matters: Big Tech uses its massive scale to drive CAC down while using its ecosystem to drive LTV up. If Meta can use AI to make ads more relevant, the LTV of a small business advertiser increases. As long as the LTV:CAC ratio is at least 3:1, the company has a "green light" to spend aggressively on growth without risking the bottom line and proves the business is sustainable and efficient.

• Design Connection: CAC goes down when the product is so intuitive that users become advocates (lowering marketing costs). LTV goes up when the product evolves with the user, preventing churn. Inclusive design and accessibility also expand the LTV by keeping the product usable for a wider, aging, or more diverse audience. 

• The Pitch: "Our focus on accessibility and error-prevention design has reduced support tickets and churn. By extending the average user's lifespan with the product by six months, we’ve significantly increased the LTV without needing to increase our marketing spend."

🚀 The Short of It Is

To lead in Big Tech, you have to move beyond being an advocate for the user and become an advocate for the business of the user.

Board members and executives don't view these five metrics as dry financial data; they view them as a roadmap for the company's survival. When you frame your design work through these lenses, explaining how a smoother onboarding drives DAU, or how a cohesive design system fuels NRR, you and your team stop being a "cost center" and start being a "growth driver."

By connecting pixels to the bottom line, you secure the influence, headcount, and budget needed to keep building the products your users love.

What’s your biggest challenge in translating your team’s design wins into business-speak?

That’s it for this week.

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to this Newsletter 

With ❤️ from Sally

⏱️ Today, in 5 Minutes or Less 

You’ll learn the "unseen" mechanics of AI-driven promotion cycles and gain a 4-slide system to prove your value when the "manager" is increasingly an algorithm.

When the System Stops Noticing You

And How to Change That …

If this resonates, you aren't alone. You are likely one of thousands of talented leaders feeling overlooked. In 2026, the game has changed: it's no longer just about your manager noticing you; it’s about the system noticing you. To break through, you have to understand that Big Tech promotions are now operationalized business decisions driven by data and, increasingly, AI.

1. Agentic Strategy & Rolling Forecasts: Companies like Google, Microsoft, and Amazon have moved from passive goal-setting to active AI goal-management. High-level objectives are now "AI-refined" through thousands of simulations. If an AI model predicts a goal is unreachable, resources are reallocated mid-quarter. If you aren't tracking your work against these Dynamic OKRs, you’re already behind.

2. The "AI Fluency" Metric: Performance is no longer just about output. 2026 research shows that Google and Amazon now factor "AI fluency" and tool usage into formal reviews. Microsoft treats AI as a "force multiplier." If you aren't quantifying how AI enhances your workflow, you’re competing against a benchmark you can’t hit.

3. The Budget and The Bell Curve: Promotion budgets are fixed and often favor "revenue-driving" teams. Product Design and UX is frequently viewed as a "cost driver" because our ROI is harder to track in real-time. To win, you have to move yourself up the Bell Curve, a system designed to over-reward the top while eliminating the bottom 10% of performers taking their compensation to pay the ones who get promoted. One way to move up the curve is to provide your manager with data that survives both human and AI scrutiny

🧰 Your New Toolkit: The 4-Slide Impact Deck

To secure that promotion, you need to bridge the gap between your design wins and what the AI system tracks. The key is real-time documentation and a proactive four-slide deck to showcase your progress. It’s a perfect strategy: it keeps your 'housekeeping' tight while building a live portfolio, playing directly to your strengths as a creative leader.

Use this Slide Deck Template for Every Project:

Slide 1: Context & AI Integration

This slide sets the context and can be used by your manager when presenting your work for promotion to their peers and seniors. It should include the following. Your name and the names of your cross-functional partners you worked with. Being inclusive demonstrates your ability to lead collaboratively. Include a professional photo of yourself. Seeing your face alongside your wins bridges the gap for executives who may not know you personally, transforming you from a "line item" into a visible, indispensable leader.

Slide 2: The "Before" and The Business "Why"

This slide should show a picture, video or prototype of the before state. Name the type of project e.g. product redesign (optimization), concept project (innovation), journey map (efficiency). It helps to use call outs to describe the problem and name your target users. For example, for this mobile banking app., users found the multi-step verification process "anxiety-inducing" and slow, leading to a 22% drop-off rate at the final confirmation screen.

Slide 3: The "After" and Strategic Altitude

This slide should include a stand alone demonstration of your final work. Put a video, prototype or screens with callouts showing how the problem was addressed and point out the key elements of your craft. Here are some examples:

• Callout A (Interaction Design): "Notice the elastic bounce on the slider, this provides tactile confirmation that the transfer is being processed, reducing 'double-tapping' errors."

• Callout B (UX Writing): "Changed 'Execute Transaction' to 'Send Money Now.' Mirroring user language reduced hesitation time by 1.5 seconds on average."

• Callout C (Motion Graphics): "The progress bar is non-linear; it moves faster at the start to create a perception of higher system performance."

Slide 4: Quantified Impact

This slide is to reflect the impact of your work that compares your "Start" with your "Finish." Use quantitative metrics that an AI resource alignment engine can ingest as well as user experience metrics and personal learning. Here are some example callouts:

Business Impact: 

• The redesigned mobile app. verification logic was moved to happen in the background, leading to a completion rate increase of 98%, and "time-to-complete" dropped from 45 seconds to 12 seconds.

User Experience Impact:

• Cognitive Load Reduction: Reduced the input fields from 8 to 3 by implementing "Smart Contacts" and predictive amount suggestions.

• Defensive Design: Integrated an "Undo" window (5-second delay) to replace the friction of traditional "Are you sure?" modals.

• Visual Hierarchy & Feedback: Used high-contrast buttons for the primary action and added a "Success" micro-interaction to provide instant psychological closure.

Personal Learning Impact:

These are the things you had to overcome and how overcoming them made your designs better. Include these to show you still have the critical thinking skills that "Knowledge Atrophy" is stripping from others. This is the way to frame you personal learning.

1. The Mistake/Assumption: "I initially thought..."

2. The Discovery: "But through [User Testing/Data/Feedback], I found..."

3. The Takeaway: "Now, I always approach [X Task] by doing [Y Action] first.

Master the Language of Leadership

If you want to secure your next promotion, it helps if you start speaking the language of the C-suite: ROI and business impact. To learn exactly how to translate your team's output into the metrics that drive executive decisions, dive into chapter six of my book, Quantifying Product Design: Key Metrics for UX Design Executives. Since its release last September, this guide has become a go-to resource for designers looking to prove their value and earn a seat at the table. Grab your copy and start measuring what matters.

The New Rules of Advancement

Don’t wait for your annual review to unveil your progress. In a world of Agentic Strategy, waiting is losing. Share your project slides the moment a project wraps to provide your manager, and the algorithms they answer to, the real-time data required to move you up the bell curve. These short decks serve as a timeless archive of your professional impact, essentially "ghostwriting" your success story for the leadership above you.

🚀 The Short of It

The gap between Senior Manager and Director in 2026 is now defined by your ability to navigate this AI-managed ecosystem. Promotions are no longer based solely on human relationships; they are about verified impact. When your boss’s boss enters a high-stakes promotion meeting, they need unshakeable confidence in your case, even if they’ve never met you. By using this 4-slide framework, you provide your advocates with standardized, high-altitude proof that makes it easy for them to fight on your behalf. You stop being viewed as a "cost driver" and emerge as the high-leverage leader the system is literally programmed to reward.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Schedule a free coaching strategy call

• Buy or give my book to your team

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

The Design Leadership Playbook

⏰ Today In 5 Minutes or Less

In five minutes or less, you will learn exactly how to audit your design process, secure your performance metrics, and navigate US and UK specific employment rights so you’re never one Slack lockout away from a career reset.

The Long Way Home

It’s been a while. I haven’t been in your inbox since January, and for good reason. I spent the end of 2025 and start of 2026 traveling extensively through California and New Mexico, a "soul-searching" trek to decide exactly where I wanted my next chapter to unfold.

While the reception from friends, mentors, and clients in the US was incredibly warm, and many expected me to stay, I hit a surprising realization. Like anyone who has lived abroad for years, I felt that familiar sense of displacement. Despite fully expecting to settle back in the US, I realized my heart (and my family) needed me back in the UK. So, that is where I’ll be based for the rest of the year.

The State of Play

Coming home has given me a "both sides of the pond" perspective on the current market, and the view is sobering. For those currently employed, the air feels heavy with performance pressure and restructuring talk. For those who have already been laid off, and I know there are many of you, I am truly sorry. My goal is to help you realign and get back to what you actually love doing.

In the spirit of being prepared (and apologies for being a bit of a "Debbie Downer"), this week’s edition is a very practical guide. Whether you feel safe or sidelined, here is how to preemptively gather what you need now to make your move to your next perfect role seamless.

Preparing for the Unthinkable

It’s a heavy time to be in Product and UX. In the last year alone, the tech sector has seen over 260,000 layoffs globally, with design and product teams often taking the hardest hits as companies "flatten" their hierarchies. In the UK, redundancy rates have climbed to their highest levels since 2020, while US tech hubs continue to see daily "restructuring" announcements.

Being laid off often happens with jarring speed. One minute you’re in a sprint planning meeting; the next, your Slack access is revoked and your laptop is a brick. If you wait until the "invite" hits your calendar, it’s already too late to save your legacy. Your instinct to prepare isn't cynical—it's professional survival.

A Note on Intellectual Property (IP): Before you save anything, check your contract. Do not download client lists, proprietary code, or trade secrets. This can trigger IT alerts, lead to legal action, or cost you your severance. Focus exclusively on "personal-professional" data: your reviews, your connections, and your design process.

🌍 The Universal Checklist (US & UK)

Regardless of where you pay taxes, these are the "Must-Dos" for every Product Design leader before you lose your SSO:

• Archive Your Design Process: Don’t just save final UI. Screenshot the "messy middle”. FigJam brainstorms, early wireframes, and sticky-note workshops. These prove how you solve problems.

• Record Prototype Videos: Record a screen-capture (with audio narration) of your best prototypes. It’s much easier to show a video in an interview than to rebuild a Figma prototype from scratch.

• The "Impact" Ledger: Write down your metrics now. Did you improve conversion by 12%? Reduce support tickets by 20%? Anonymize user research quotes that prove your design solved a real pain point.

• Evidence of Collaboration: Screenshot "kudos" from developers and PMs. If a lead engineer thanked you for a clean handoff, that is your best future testimonial.

• Inventory Your Tech Stack: List the tools you’ve mastered (e.g., Mixpanel, Hotjar, Storybook, Zeroheight). Being an "expert-level" user is a major selling point in a tight market.

• BCC Your Personal Email: For non-sensitive, purely personal emails (like praise from a client), BCC your personal account. Avoid bulk-downloading files, which often triggers security flags.

• Digital & Physical Housekeeping: Clear your browser history and saved personal passwords. Start taking personal items (plants, books, photos) home now so you aren't carrying a "box of shame" later.

🇺🇸 The United States Checklist

In the US, "Employment at Will" means you can be locked out in minutes. You must act today.

• Tax & Pay Records: Download your last 3 months of pay stubs and your most recent W-2. Ensure you have a personal login for your payroll portal (ADP, Workday) that doesn't rely on company email.

• FSA/HSA Management: Use your FSA funds now. If you have a balance, buy prescriptions or medical supplies today. Once you're out, that money is usually gone. Note your HSA account details; that money stays with you.

• Benefit Summaries: Download your Summary of Benefits (Health, Dental, Vision) and your 401(k) statements.

• COBRA vs. Marketplace: Design roles currently take 3–6 months to land. Research the cost of COBRA versus a plan on the Healthcare.gov marketplace so you aren't surprised by the premium.

• Portfolio Redaction: US contracts are aggressive about "Work for Hire." Ensure any work you take is destined for a password-protected site or is sufficiently redacted to protect company secrets.

🇬🇧 The United Kingdom Checklist

The UK offers stronger redundancy protections, but you need to know your rights to leverage them.

• Statutory Rights: If you’ve been at the company for over 2 years, you are legally entitled to Statutory Redundancy Pay. Use the GOV.UK calculator to know your number.

• The P60 & P45: Ensure you have your P60s. Your employer must issue a P45 upon your departure; keep a close eye on this for your next role.

• Consultation & Consent: If 20+ people are being let go, there is a legal consultation period (30–90 days). Use this time to ask your manager for written permission to use specific projects in your private portfolio.

• Garden Leave Strategy: Check if your contract has a "Garden Leave" clause. If you are paid to stay home during your notice period, use those weeks to update your case studies while the "why" behind your decisions is still fresh.

• Pension Tracking: Note your provider (Nest, People’s Pension, etc.) and your policy number. It’s easy to lose track of these small pots once you move on.

• LinkedIn Networking: UK recruiters are heavily LinkedIn-reliant. Export your Outlook contacts to a .CSV file now so you can reconnect with colleagues and vendors on your own terms.

Leading by Design: The Insider's Handbook for Tech Leadership

🚀 The Short of It Is

The tech landscape is shifting beneath our feet, and while we can’t control corporate restructuring, we can control our readiness. Your "survival kit" isn't just about saving files; it’s about preserving the evidence of your impact. The "messy middle" of your process, the hard metrics of your success, and the professional relationships you’ve built.

Whether you are navigating the "at-will" speed of the US market or the statutory protections of the UK, the goal is the same: to ensure that when one door closes, you have everything you need to walk confidently through the next one.

Don't wait for the calendar invite; start your housekeeping today.!

PS: Would you like to receive more career strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

A blueprint for career strategies in product design leadership

⏰ Today In 5 Minutes or Less

A deep dive into how the team at Artefact  transformed agency friction into a global resource management tool, proving that the best products solve your own "Big Friction."

Case Study: 10,000ft

This week, I’m exploring the career of Rob Girling, co-founder of the iconic consultancy Artefact and the co-creator of the resource management tool 10,000ft. For those looking to dive deeper into our whole conversation, you can find the complete interview in my book, Leading by Design.

Rob’s journey is a masterclass in moving from a "service" mindset to a "strategic product" space. 10,000ft was born not from a desire for market disruption, but from the raw pain of managing a growing team of 30 designers on a spreadsheet that was starting to break. It was designed to solve the "clunky spreadsheet" problem for creative agencies and distributed tech teams who need a high-level perspective on organizational health.

10,000ft was acquired by Smartsheet in 2019. Separately, Smartsheet was acquired by Blackstone and Vista Equity Partners for $8.4 billion deal.

Snapshot of the User Interface Design from 10,000ft

1. “Build What You Know” Principle

Between 2006 and 2011, Rob and the Artefact team, led by co-creator Martijn van Tilburg and business partner Gavin Kelly, were swept up in a wave of design optimism. Gavin, an Artefact co-founder, served as the "third leg" of the 10,000ft stool, providing the essential strategic balance the project needed.

Despite their design pedigree, the team spent years chasing "snazzy" concepts and "magic" prototypes that failed to gain traction. The missing ingredient? A lived-in, deep understanding of the problem space.

The breakthrough happened when they looked inward at their own friction. As Rob explains:

The Insight: Your most valuable product opportunity is rarely a "Blue Sky" idea; it is likely the problem you face every single day. For the 10,000ft team, it was the breakdown of resource management.

Action for Leaders: Stop hunting for "The Big Idea" and start auditing "The Big Friction." What is the one recurring task that your team complains about every Friday? That friction isn't just a nuisance; maybe it’s your product.

2. Spotting the "Spreadsheet Breaking Point"

A spreadsheet that works perfectly for 10 people; It’s "clunky" but functional for 20; at 30 people, it becomes a liability. When you reach a "breaking point," you have two choices:

• The Service Choice: Hire an operations person to manage the mess.

• The Product Choice: Design a system that automates the mess.

Rob, Martijn, Gavin, and team chose the latter. They realized that if their agency needed a high-altitude view of project workflows, every other creative organization on the planet probably did too. They were right! I used 10,000ft to manage the workflow and visibility into our impact as a business driver as Chief Design Officer for [24]7.AI.

3. From "Optimistic Prototyping" to "Technical Empathy"

One of the most profound insights for the team was the gap between a vision and a viable business. The team realized that while designers excel at the "Front-End", they lacked visibility into the "Back-End" (the support infrastructure and the sales cycle).

Rob describes this shift as a move from arrogant design to technical empathy:

4. Designing the Culture as a Product

One of the most compelling takeaways from the 10,000ft story is that the software was a direct manifestation of Artefact’s internal culture. Rob and Gavin built Artefact as a "flat" organization that rejected traditional micromanagement. Consequently, 10,000ft was designed with a "high-altitude" view where every team member could see the entire landscape of the company’s work.

The Leadership Lesson: Software is "Coded Culture." When you build a tool, you are essentially coding your culture.

• If you design for transparency, you are advocating for a high-trust culture.

• If you design for "locked" permissions, you are reinforcing a culture of gatekeeping.

Leading by Design: The Insider's Handbook for Tech Leadership

🚀 The Short of It Is

If you are an aspiring design leader looking to build successful internal products, here is the essential playbook for how to do this:

1. Audit Your Own Friction: Look for the "Big Friction", that recurring, painful task your team handles via a breaking spreadsheet.

2. Build What You Know: Success comes from a lived-in understanding. Even as UX designers (like Martijn and Rob), your strongest tool is your own frustration.

3. Find Your "Third Leg": Don't go it alone. Just as Gavin Kelly and Rob provided the necessary foundational support for Martijn and the team, find partners who balance your design vision with business and strategic rigor.

4. Practice Technical Empathy: Move beyond "snazzy" prototypes. Respect the complexities of engineering and scaling.

5. The "Functional Hack" Strategy: Don't wait for perfection. Build the simplest version that solves the core problem and get it into users' hands immediately.

The full interview with Rob Girling, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

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With ❤️ from Sally

⏰ Today in 5 Minutes or Less

By reading this, you will identify the four mindset shifts necessary to move from designing interfaces to directing product strategy and market viability.

From UX Lead to Product Manager: The Strategic Pivot

The transition from UX Lead to Product Management (PM) is one of the most natural, yet culturally jarring, shifts a design leader can make. While you already possess the empathy and research rigor required for success, moving into a PM role requires shifting your focus from the "Guardian of the User" to the "Guardian of the Business."

How do you turn UX expertise into a seat at the leadership table? Lynn Bacigalupo, Global Product Manager at Icomera, has the roadmap. In this feature, she breaks down her transition from design strategy to overseeing cutting-edge AI transit solutions. For the complete masterclass on her leadership philosophy, check out the full interview in “Leading by Design: The Insiders’ Playbook to Tech Leadership”.

Inside the Roadmap: How Lynn Bacigalupo Translates UX Strategy into High-Impact PM

Transitioning into PM isn't about leaving design behind; it’s about applying design to the business model itself. While UX Designers and Product Managers work in the same trenches, their North Stars differ.

As Lynn notes, "In both UX and product management, the focus is on understanding the user's needs... but the cultural shift has been noticeable." To successfully transition, you must move from the "How" (the interface, the flow, the interaction) to the "Why" and "What" (the market fit, the ROI, and the roadmap).

UX vs. PM: Strategic Priorities

Step 1: Broaden Your Time Horizon

One of the most significant adjustments Lynn highlights is the shift in perspective regarding time. "When I was working hands-on, my focus was on the immediate deadline," she explains. "As a leader, my thinking often extends to a five-year timeframe."

As a UX Lead, you likely think in sprints or release cycles. As a PM, you must believe in market cycles. In Lynn’s world of rail transit, infrastructure lasts decades, but tech evolves in months. A PM must navigate this "friction," ensuring that a product launched today won't be obsolete by the time the hardware is fully deployed.

Step 2: From UX Research to Market Intelligence

Her background in research strategy smoothed Lynn’s transition. However, PM research goes beyond usability. It involves understanding industry-wide shifts.

For example, Lynn leverages industry studies to identify where AI can improve rail operations. She isn't just asking if a button is clickable; she's asking if Video-based AI is the most cost-effective way for transit agencies to report passenger counts to the government.

To move into PM, you will measure efficiency and viability alongside usability.

• UX View: "Can the user complete this task?"

• PM View: "Does completing this task reduce operational costs for the client?"

Sally and Lynn, The UN Plaza, San Francisco, December 2025

Step 3: Master the "Internal" Customer Journey

A pivotal moment in Lynn’s PM career involved improving internal network operations tools. She realized that if the internal teams couldn't support the product, the external customer experience would eventually fail.

She approached this with a "consultant mindset", gathering stakeholders, identifying pain points, and presenting solutions. This is a UX strategy applied to Organizational Design. To be an excellent PM, you treat your developers, sales teams, and support staff as users. Lynn’s Advice for Collaboration:

Step 4: Embracing "Hybrid" Methodologies

As a UX Lead, you might be a devotee of Agile or Lean. As a PM, you have to be a pragmatist. Lynn notes that while Icomera uses lean startup methods, the realities of complex hardware and long backlogs often require a hybrid approach.

"Launching involves much more than simply releasing the product," Lynn cautions. You have to consider:

• Can the project engineers implement it?

• Does the service team know how to support it?

• Is there robust monitoring in place?

A PM ensures the entire ecosystem is ready, not just the code.

Step 5: Leading with Values

Perhaps the most profound insight Lynn shares is how her leadership was shaped by working with a development team in Ukraine. This experience reinforced Value-Based Leadership.

In the transition from individual contributor to PM, it is easy to become obsessed with "output." Lynn argues for a focus on "people as individuals." This empathy, a core UX trait, is actually a superpower in Product Management. It allows you to build the trust needed to navigate the "unstructured" ways in which many organizations actually make decisions.

Leading by Design: The Insider's Handbook for Tech Leadership

How to Start Your Transition from UX to PM Today

If you are currently a UX Lead looking to move into Product, here are three actionable steps based on Lynn’s experience:

1. Volunteer for a "Non-Design" Problem: Like Lynn’s internal tools project, find a bottleneck in your company’s operations and lead the discovery phase to fix it.

2. Learn the Language of Stakeholders: Start attending meetings with Sales, Marketing, and Finance. Understand what metrics they care about (Revenue, Churn, ROI) and map your design wins to those goals.

3. Frame the "Why": In your next handoff, don't just explain the user flow. Explain the market necessity. Why is the business investing $100k in developer hours for this specific feature right now?

The Short of It Is 🚀 

The transition from UX to PM isn't about losing your design soul; it's about giving your design skills a larger playground.

The full interview with  Lynn Bacigalupo, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

A blueprint for career strategies in product design leadership

⏰ Today in 5 Minutes or Less

How do you balance high-level design with engineering reality? This week, Ajay Thakur (Chief Information Officer at Movius and former Head of Cognitive Computing and Staff Engineer at Uber) shares a deep dive into bridging the gap between aesthetic vision and technical feasibility.

The Evolution of the Technical Product Designer

As design leaders, we often focus on "user delight" and "user journey." However, in the high-stakes world of global scale, think Uber-level complexity, delight, and a golden path journey without feasibility will stall.

If you’ve ever had a vision stalled because "the API doesn't support it" or "the bandwidth costs are too high," you’ve hit the technical wall. To lead modern product design teams effectively, moving beyond the "design specification handoff" culture is essential.

Empowering creative teams to learn about the technical levers that determine whether a product succeeds or fails in production is a step toward increasing the department’s return on investment (ROI) for the business it serves.

In a featured interview from my book, Leading by Design, Ajay offers an invaluable perspective on the synergy between our disciplines, arguing that the next generation of product designers looks beyond the interface to understand the "machinery" that brings their visions to life.

The Designer’s New Toolkit: Technical Empathy

Ajay’s philosophy is rooted in technical empathy. At Uber, where real-time data is the heartbeat of the app, he views designers as vital partners when they possess a deep understanding of the system's constraints.

For Ajay, the "magic" of a customer experience is actually the result of rigorous negotiation between design ambition and engineering reality. When designers understand the "Why" behind a technical "No," they can pivot to a "How" that actually works.

3 Key Ideas to Mastering Technical Design

Using Ajay’s insights, here are three ways you can lead your team toward technical fluency:

1. Map the "Data Journey" Before the User Journey

Ajay emphasizes data availability. In real-time apps, if data is slow or inaccessible, your design fails.

• The Approach: Don't just design the "happy path." Ask your engineers: "What is the fallback state if this API call takes longer than two seconds?" or "Do we actually have access to this user data in real-time?" Designing for data latency is just as important as creating the user interface (UI).

2. Design for "Minimal-Regret" (The Agile Mindset)

Ajay favors the Agile Manifesto for its speed and "minimal-regret" delivery. He argues that "less is more" often leads to better outcomes and stability.

• The Approach: Challenge your team to identify the "heaviest" part of their design. If a feature requires a custom API or excessive network bandwidth, ask whether there is a way to achieve the same user goal using existing components or proven frameworks. This reduces friction and speeds up velocity.

3. Transition from Mockups to "Technical Logic."

Ajay highlights the importance of interaction flowcharts and documenting the "Why" behind choices. With the rise of AI, the gap between design and code is shrinking.

• The Approach: Encourage your designers to think in logic, not just layouts. As AI-powered interfaces begin to anticipate user needs, designers will be defining the rules and predictions the UI should make. A designer who can write a working prototype or prompt an AI to generate functional code is no longer just a "design" partner; they are a technical design lead.

Leading by Design: The Insider's Handbook for Tech Leadership

The Future: Designer-Developer Synergy

When AI can turn a single engineer into a team of hundreds, designers don't become less relevant; their technical literacy becomes the differentiator. By bridging the gap between design and code, we move toward a future where designers aren't just drawing interfaces, but directing AI-driven logic and producing functional prototypes.

But what, if anything, is holding you back? Samira Rahimi, Head of Platform Experiences Design at Uber, hits the nail on the head in her article “The Parts of Your Job AI Should Absolutely Steal.” She asks: “What stops designers—tools, or fear?”

If you’re leading a design team today, the hard part isn’t the tools; it’s the mindset. For years, designers were taught that the "machinery" wasn't their job. That legacy is the real blocker. To move forward, we have to normalize technical experimentation, making it low-risk and, eventually, a core part of the creative process.

Your Challenge: Confront the "Technical Wall"

Overcoming the fear starts with a conversation. Ajay Thakur identified his top three constraints as API limitations, bandwidth, and data availability.

What are yours?

Does your team have a framework for discussing these technical levers, or do you hit a "wall" every time you move from Figma to production? Leave a comment and let me know how you are encouraging your team to move beyond pixels and into the code.

The full interview with Ajay Thakur, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

A blueprint for career strategies in product and design leadership.

⏰ Today in 5 Minutes or Less

Learn how Anshuman Kumar, former SVP of Design at Asana, drove $10M in annual recurring revenue by gamifying product optimization and owning the P&L.

The Evolution of Design Executive Anshuman Kumar

For many designers, the transition from practitioner to manager feels like a natural progression of craft. But for Anshuman Kumar, former SVP and Head of Design at Asana, the leap from manager to executive required a fundamental shift in perspective. It wasn't just about leading a team of 100+ designers; it was about shifting the "output" of design from pixels to business decisions to maximize design leadership and business ROI. As Anshuman shares in my book Leading by Design, becoming an executive meant moving beyond the screen to influence the company's financial trajectory.

In his career journey from Yahoo to Google and to the helm of Asana’s design org, Anshuman mastered a skill many design leaders struggle with: speaking the language of the business. This shift is essential for bridging the gap between UX and the bottom line.

One of the most profound realizations he had was the change in "time horizon." While a manager might focus on the following product cycle, an executive must look much further ahead; at Google, he lived six months in the future, but at Asana, his horizon moved to three years, allowing him to drive product optimization and gamification strategies that resulted in a staggering $10M revenue impact.

This shift meant moving away from the "unannounced Figma visit," which he learned can accidentally intimidate some designers, and moving toward multi-million-dollar budget accountability and long-term organizational health.

📖 Case Study

Gamifying the P&L to Drive $10 Million in ARR

The most striking example of his business-first leadership occurred when Asana set Annual Recurring Revenue (ARR) as a North Star for R&D. Anshuman saw this as an opportunity to prove his design team's worth in a language the board of directors would understand.

1. Identifying "Revenue-Sensitive" Surfaces 💰

Drawing on his early career experience at Yahoo, where changing a font size on an ad product could immediately impact the bottom line, Anshuman knew that certain "surfaces" (user interfaces) were more sensitive than others. He focused his team on payments, new user adoption, and retention.

2. Doing 30% of the Work for Others 👷🏾👷🏾

Instead of waiting for permission, his team audited critical surfaces and identified every UX bug that could be hindering conversion. They identified problems and provided solutions. From the documented list of solutions, he invited the stakeholders to choose what to optimize.

3. Gamification and the Leaderboard 🎲

To drive momentum, they created a leaderboard to track experiments conducted by cross-functional teams. This turned a technical backlog into a competitive game, motivating teams to fix "P2" (moderate-to-high-priority bugs affecting core functions or user experience) and "P3" (low-priority minor bugs, cosmetic glitches, or single-user problems) that had been ignored for months. 

4. The Result: A $10 Million Success 🤑

When Anshuman approached the Chief Product Officer, he didn't talk about "user delight" or "aesthetic consistency." He said, "We’re going to make $12 million in one year." By the end of the year, the design-led optimization initiative had driven $10 million in ARR (annual recurring revenue). More importantly, it sparked a cultural shift in which the entire R&D team realized that the quality of the product user experience is a direct driver of business growth.

Lessons for Aspiring Design Executives

Anshuman’s success offers a blueprint for design leaders looking to claim a seat at the executive table:

• Own the P&L: Don't wait for someone to hand you financial responsibility. Set ambitious targets, tie your design goals to revenue or retention, and be willing to be measured by those numbers.

• Avoid False Trade-offs: An executive’s job is to find the "third way" when business needs and design vision seem to conflict.

Leading by Design: The Insider's Handbook for Tech Leadership

The Short of It Is 🚀

A design leader's journey at the highest level isn't about protecting the "sanctity" of the craft from the "coldness" of business. It’s about using the design process to solve the business’s most complex problems. When you can walk into a room and tie a UX improvement to a $10 million revenue bump, you aren't only a designer, but a business leader who happens to use design as your primary tool.

The full interview with Anshuman Kumar, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

Welcome to Leading by Design!

Introducing Julie Baher

The Executive Who Champions Passion as a Strategic Asset

Today I want to introduce you to someone who has built a remarkable career on the principle that passion is a strategic asset. Julie Baher is a Digital Health Executive and veteran of the UX community. Her journey from designer to executive illustrates how connecting your authentic self to your professional pursuits isn't just about job satisfaction, it's about achieving maximum impact and earning a real voice at the strategic table. To understand her perspective, you need to know a bit about her background

That connection to medicine and science, seamlessly woven together with her technical and design skills, became the powerful strategic foundation for her ultimate executive role. Julie has written about this in her LinkedIn article, Finding Your Passion at Work and in an interview in my book Leading by Design. Let’s dive into her insights.

The Foundation: Combining Disparate Interests

Julie's career was built on a series of purposeful convergences. The first lesson for design leaders is to stop viewing your skills as linear. Julie’s journey into User Experience (UX) was fueled by a lifelong fascination with combining seemingly disparate fields. She realized her passion lay in the “intersection of art and problem-solving,” specifically, the desire to combine her “love of math and creativity.”

This fascination quickly translated into a professional philosophy: “Once I discovered graphic design, I thought, 'Why isn't this taught in schools?' It's applied art, not fine art. You're not trying to be a Rembrandt but creating practical, useful things. And I'm a practical person.”

This insight, that design is fundamentally about creating practical, functional solutions is the core value that anchored her career. It allowed her to focus on its problem-solving application.

Jule with Sally, December 2025, Santa Fe, New Mexico

The Strategic Act of Value Alignment

Julie emphasizes the importance of "finding companies where her values align with the organization's mission." She has consistently selected organizations—from Adobe to Citrix to Myriad and now GeneDx, where she could genuinely connect her interests to the mission:

• Helping Creatives: At Adobe, she connected with her love of darkroom photography and desktop publishing to help creative professionals.

• Supporting IT: At Citrix, her background in building computers and IT allowed her to connect with IT customers.

• Improving Human Health: This is where the long-shelved passion for science finally became central. At Illumina, Myriad and now GeneDx she could integrate her biology background, interest in medicine, and software design skills to help scientists, doctors, and patients through genetic insights.

This deep alignment is what enabled her to “excel as an executive leader.” She isn’t just performing a job; she is fulfilling a deeply personal mission.

For design leaders, the transition to the executive level often means a battle for respect and recognition. Julie notes the common pitfall in some tech environments: UX is often marginalized, brought in late, and viewed as providing mere “window dressing”. However, her value-aligned career in the life sciences provided the perfect counter-narrative, proving that passion directly leads to influence.

The 'Big Tent' Advantage

In tech, the product story often revolves around an engineer and a product manager. Julie found that the life sciences industry naturally operates with a “big tent” approach.

This environment, where her passion for science gave her instant credibility, allowed her to achieve her ultimate goal: positioning herself as a valuable strategic contributor. She realized that to fully embody the role of a Vice President, she needed to shift her mindset “away from simply being the UX leader” and toward broader strategy. Her foundational passion gave her the conviction to “be more assertive about my role” and avoid being undervalued.

Systemic Problem-Solving

Her deep interest in understanding the system is another critical facet of her passion. As a child, she loved Richard Scarry’s book, What Do People Do All Day? This childhood curiosity grew into a professional strength: "I like knowing how things work and seeing the systems at play." And this this translated into a unique ability to tackle enormous, complex scopes. For example as VP Digital Health for Product Management and User Experience Design for Myriad:

• Integrated Leadership: She led the product management team in addition to UX. This dual role gave her the necessary “authority to comment on development work and other areas” and ensure UX is involved in the entire product stack, aligning design priorities with the overall business vision.

• Design Thinking for Systems: Her team used visual mapping, workflow analysis, and journey mapping to understand the entire “Jenga tower” of the ecosystem—including customer service, billing, and medical professionals—before making changes.

The Takeaway

Julie Baher's journey powerfully illustrates this truth: Passion is not a luxury in executive leadership; it is your core strategic asset.

Think about it: genuine enthusiasm provides the kind of clarity and conviction that mere experience cannot.

• It gives you the clarity to choose the right companies—those missions and cultures that deeply resonate with your purpose.

• It builds the credibility necessary to be a truly strategic contributor, allowing you to speak with authority that transcends departmental silos.

• Most importantly, it arms you with the conviction needed to assert the value of design against entrenched organizational practices and short-sighted thinking.

Your Multifaceted Advantage

Your unique combination of interests whether you blend graphic design and mathematics, or biology and software engineering is not a distraction to be minimized. It is the strategic narrative that will define your executive success. It's the unique lens through which you see problems and solutions that no one else can match.

Don't settle for environments that merely tolerate your skills. Seek the organizations that actively reward your multifaceted interests and allow you to align your deepest personal values with their mission.

When you embrace this intersection of passion and skill you move beyond being a highly effective team leader to becoming a visionary strategic executive who truly shapes the future of the business.

What Drives You?

What is the unique, driving passion, the combination of skills and interests that motivates you to do the work you do today, and how are you leveraging it to move your company's mission forward?

The full interview with Julie Baher, along with insights from many other design and tech executives, is available in the book, Leading by Design: The Insider's Handbook for Tech Leadership, on Amazon.

That's it for this week!

PS: Would you like to receive more leadership strategies?

Here are a few ways I can support you:

• Schedule a free coaching strategy call

• Buy or gift my book 

• Subscribe to this Newsletter 

With ❤️ from Sally

You received this email because you subscribed to or bought one of our products.

Thank you! 

© 2026 Sally Grisedale, Clear Channel Coaching.

Today, in 5 Minutes or Less ⏱️

You will learn two essential AI strategies that top design leaders use to secure their team's value, drive business efficiency, and navigate the current wave of tech layoffs.

Did You Know 🔎 

Intense contraction and strategic realignment in the tech industry in the US have led to significant ongoing layoffs in the tech sector, according to the official count.

• 2024 = 95,667 layoffs

• 2025 = 206,102 layoffs

• 2026 = Continued volatility. 58% of US business leaders  anticipate more layoffs driven by a permanent shift in staffing needs. AI is the Force Multiplier: 37% of companies expect to replace roles with AI by the end of 2026. 

According to an HBR report, half of a skill's value is lost within 2.5 years. This demands a new skill set to remain relevant, making continuous strategic evolution a prerequisite for survival during periods of organizational upheaval.

The data underscores that if you work in tech as a design leader, your priority for the next year is radical reinvention of how you define, communicate, and execute your work to maximize your value in an AI-driven, data-driven, speed-to-market-obsessed environment.

The Steps You Can Take to Navigate Org. Change with AI

The holiday season, starting around Thanksgiving, is when executive teams finalize next year's budgets, headcount, and often, the inevitable cost-cutting layoffs. This "scorched earth" corporate thinking—designed to hit short-term quarterly targets by shifting salaries from laid-off staff to top performers—is a reality I've seen play out at Apple, Yahoo, and Meta.

To insulate your team and make an undeniable business case for their continued existence, here are two core AI strategies you can adopt to keep your design function intact.

Integrate AI to Enhance Design Efficiency and Scale

To demonstrate efficiency in your organization, integrate AI tools to accelerate, improve, and scale design output. For example:

• Automate Tedious Tasks: Implement AI tools (like generative AI for rough drafts or predictive tools) to automate repetitive, low-value tasks (e.g., basic layout variations, repetitive image resizing, or generating design spec documentation). This frees up designers to focus on complex problem-solving and strategic thinking.

• Create AI-Powered Design Systems: Use AI to make the design system smarter. This could involve using AI to automatically audit accessibility compliance, predict optimal component usage based on context, or quickly generate localized variations of UI elements, ensuring consistency and reducing manual effort across the entire product suite.

• Accelerate Prototyping and Testing: Leverage AI to quickly generate diverse prototypes and simulate user behavior at scale, significantly reducing the time spent on manual A/B testing setup and analysis, leading to faster iteration cycles.

Drive Strategic Value by Leveraging AI for User Insight and Personalization

The second, more critical step is to leverage AI to unlock new avenues of business value and strategic impact. This involves shifting the design focus from merely building interfaces to designing intelligent, highly personalized, and data-driven experiences.

• Design for Intelligent Experiences: Focus on how AI can create new, valuable product features that are useful, transparent, and trustworthy. For example, designing the inputs, outputs, and feedback loops for AI features such as personalization engines, intelligent recommendations, and automated workflows. 

• Translate AI Insights into Actionable Design: Make data-backed decisions that directly improve key business metrics like conversion, retention, and time-to-task completion, and do this using AI to synthesize user data (e.g., behavior patterns, sentiment analysis, task success rates) into clear, actionable design insights.

• Establish Ethical and Responsible AI Design Guardrails: To protect long-term business value and user trust, you must help the company define policies on data privacy, mitigate algorithmic bias, and ensure transparency into how AI influences the user experience. If you lack visibility into this work, ask for it. If your company hasn't started addressing these issues, take charge and lead it. Owning the Service-Level Agreements (SLAs) for ethical AI and experience quality is how you acquire influence and power within the company.

The Short Of It 💥 

Ultimately, protecting your team from vulnerability to layoffs this holiday season requires you to recast and actively promote your essential value proposition. This means achieving immediate fluency in the strategic deployment of AI. This is achieved through two critical, integrated actions:

1. Integrate AI to Enhance Design Efficiency and Scale: Use AI tools to accelerate and expand your creative output.

2. Drive Strategic Value by Leveraging AI for User Insight and Personalization: Apply AI to data to deliver highly personalized experiences that yield significant business impact.

That's it for this week!

PS: Would you like to receive more leadership strategies? Here are three ways you can do that.

• Schedule a free coaching strategy call

• Buy, gift, and review my book 

• Subscribe to this Newsletter

With ❤️ from Sally

PPS Would you like to receive more leadership strategies?

Here are a few ways I can help:

• Book a free coaching session for 30 min. strategy call

• Apply to sponsor an upcoming issue of Leading by Design

• Contact me with feedback and suggestions for future topics  

Welcome to Leading by Design!

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Today, in 5 Minutes or Less ⏰

You’ll learn the mindset shift that turns creative focus into leadership success, how to overcome impostor syndrome by focusing on judgment rather than expertise, and the strategy for creating an experience-delivery system (EDS) that guarantees executive buy-in.

Executive Insight with Phil Clevenger 🔍

At the time of our interview, Phil Clevenger was the Vice President of Product Experience at DocuSign, leading a team of over 150 professionals. His deep experience includes 17 years at Adobe, where he designed the first versions of Adobe Lightroom, and a pivotal early career mentored by the renowned designer Kai Krause, who taught him the enduring lessons he uses to shape digital experiences today. The full interview with Phil is included in my book, Leading by Design, in the chapter "How to Get the Top Job."

The Individual Contributor (IC)-to-Leader Shift

“As you transition from Individual Contributor (IC) to a managerial role, you face a profound challenge: shifting from a "24-hour cycle of worry and stress" focused on your own deliverables to a leader responsible for political standing as well as securing and directing resources. One salient mindset shift is to be consistently cultivating your "oxygen supply" -  the executive sponsorship that validates design as a business asset, rather than a cost center.

Phil’s Executive's Thesis

Phil's thesis is that leadership is a tremendous liberation from being a "prisoner of me" (the self-oriented designer) to being focused on service and scale. The reward of an executive role is having "far more impact on a broader scale than I ever did as an individual contributor" by elevating others and using design judgment and resources to solve large-scale business problems.

1. The Strategic Translation: Linking Design to Revenue

Phil Clevenger's strategy starts with a clear mandate: understand the business's financial goals, then build a design strategy to meet them.

Example Problem: Adobe's SaaS products were largely vertical and often not well integrated for a variety of reasons. The business needed to break them into flexible, composable UX microservices to increase revenue and gain a competitive advantage—allowing for custom sales bundles and bespoke customer environments.

The Design Solution: Phil and his team created what they called an "Experience Delivery System." This system, a large step beyond a conventional design system, was a set of standards and infrastructure meta-components necessary to deliver a unified, frictionless experience across all existing services and to embrace new or incoming services. Design built the foundation that enabled the new financial strategy.

Phil and Sally. Nov 19 2025, San Francisco

2. Translating the Business Goal into a Design Imperative

Phil recognized that simply breaking apart the back-end code would create a Frankenstein's monster on the front end if design didn't intervene. His design objective was twofold:

• Improve CX (Customer Experience): Ensure the experience matches the specific needs of each customer (addressing the "bespoke environment" goal).

• Reduce Friction: Drastically reduce the learning curve for users by creating a frictionless, consistently understandable user experience, regardless of which services they are utilizing.

3. The Solution: The Experience Delivery System (EDS)

The EDS was the strategic design initiative Phil championed to solve the technical and customer-facing problems simultaneously. It went beyond the scope of a typical Design System:

4. Gaining Buy-in: Prioritizing the Invisible Work

Phil's insight lay in how he advocated for this major undertaking. Instead of simply asking for budget to "build a design system" (which sounds like an internal expense to finance), he framed the EDS as the critical enabler for the C-suite's explicit revenue goal:

• The Argument: "We cannot achieve the goal of flexible, integrated services and increased competitive advantage unless the customer experience is equally seamless. The Experience Delivery System (EDS)  is not a design tool; it is the necessary foundation for delivering the bespoke, frictionless experience that will drive user adoption and retention across our new product architecture."

• The Priority: He ensured the EDS was a top-tier priority on the design strategy sheet, directly linking its objectives and milestones to the overarching Adobe business objective. Phil ensured the design team "knew and needed to do" this work to accomplish the stated business goals, securing the mandate without waiting for the business to explicitly request the infrastructure.

By connecting the EDS to the quantifiable goals of increasing revenue and strengthening competitive advantage (via better CX and faster development), Phil transformed a foundational design project into an indispensable business strategy project.

Use Phil's Tips Yourself: 4 Tactical Steps for Design Leaders 🪜

1. Focus on Service to Find Success

When worried about losing your creative spark, shift your focus from self-orientation to kindness and empathy for your team's growth, which Phil found to be a massive source of personal energy and inspiration. 

2. Lead with Judgment over Expertise

When leading non-design teams (e.g., Research, Content Strategy), overcome impostor syndrome by remembering that successful leaders, like politicians, rely on informed judgment and the specialized knowledge of their staff, not personal expertise.

3. Cultivate Your "Oxygen Supply”

Recognize that executive sponsorship is crucial. If key leaders retire or move on, the environment can shift, forcing you to "spend time educating them, proving yourself all over again”. Always be building and maintaining connections across your organization.

4. Determine Resourcing Scientifically

“Avoid the "Wicked Witch's throne room" trap of fixed ratios. Instead, focus on the ratio of designers to feature-level Product Managers, starting with a 1:1 assumption and adjusting based on transparent project scope and needs.

5. Apply the Right Metrics & Measurement

How the leader connects design work to business KPIs; Phil assesses the design team not on constant shipping speed, or whether designs get shipped at all, but on two equally important factors: 

1) The quality of their work and 

2) Their ability to build positive relationships. 

“The ultimate measurement of a kick-ass team is the positive impact seen in the business, which is evident when engineering or product management partners voluntarily reach out with gratitude and appreciation for the design contribution and collaboration."

Phil’s Leadership Lesson ✍🏽

The essential mindset shift for an executive leader is to "free yourself of some of the fears" you had earlier in your career. Stop worrying about being right or being the best. Instead, "lean back a little bit, take it all in, listen hard, use your best judgment, delegate well, empower others, and move to the next thing." This non-personal approach allows you to focus on the work as a role, not a personal drama, and enables greater impact while reducing stress.

Phil Clevenger’s experience teaches us that the highest form of design is leading people and strategy. His insights are a roadmap for turning your fear into freedom and your function into a true business driver. 

Dive deeper into Phil Clevenger's full interview in my book, "Leading by Design: The Insiders Playbook for Tech Leadership.”  Order your copy today! 

That's it for this week!

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With ❤️ from Sally