Hi {{ first name | there }},

Last week, I had the opportunity to speak at Matik's AI + Post Sales Summit, where I shared how I use AI to build strategic Success Plans.

If you missed it, you can watch my session here.

You can also watch all summit sessions here. (Highly recommend them)

The event brought together Customer Success, Services, Operations, and Revenue leaders who are actively using AI in their day-to-day work.

I've spent the last two years experimenting with AI to improve how I research customers, prepare for executive conversations, analyze data, and build Success Plans.

So when I saw the lineup for this summit, I knew I had to attend.

One thing stood out to me almost immediately.

Many of the presenters openly admitted they don't have technical backgrounds.

They're not software engineers; most don't know how to code, and yet… they're building agents, automations, workflows, and internal tools.

The common thread wasn't technical expertise; it was a willingness to experiment.

When they got stuck, they used AI to help them get unstuck.

When something didn't work, they adjusted their approach and tried again.

And again.

And again.

As I listened to the sessions, I found myself asking a simple question:

How can I apply this to my role as a Strategic CSM?

Because the truth is, I'm still very early in my AI journey.

Yes, I use AI every day to:

• Research customers

• Analyze 10-K reports

• Prepare for executive meetings

• Build Success Plans

• Generate discovery questions

• Analyze data and identify opportunities

But many of those workflows are still surprisingly manual.

And that's what I'm excited to change.

The Summit gave me a long list of ideas I want to explore over the next few months, but here are my top 4.

Automatically updating Success Plans

Today, AI helps me build Success Plans significantly faster.

Over the last two years, I've developed prompts and workflows that help me accelerate research, executive stakeholder analysis, discovery preparation, and success planning.

Many of those workflows eventually became part of my Success Plan Playbook.

But after every discovery session, I'm still manually updating documents, capturing business outcomes, documenting success metrics, and tracking milestones.

What if that process happened automatically?

I imagine finishing a discovery call and having AI update the Success Plan with new challenges, business outcomes, success metrics, stakeholders, risks, and milestones.

That's a workflow I'd love to eliminate. Wouldn’t you?

Building a customer intelligence engine

Research is the foundation of every Success Plan I build, and Step 1 of the Success Plan Playbook.

It's also one of the most time-intensive parts of the process.

Today, I still need to search for company updates, earnings reports, leadership changes, acquisitions, and industry news.

What if AI continuously monitored those sources for me?

What if every week I received a briefing highlighting the most important developments across my strategic accounts and explaining why they matter and how to tie them back to their business outcomes?

Creating a Customer 360 view

This one might be the most impactful, and oh boy… one that excites me the most!

Imagine automatically storing every customer interaction in a single place.

• Sales conversations.

• Demo notes.

• Implementation discussions.

• Support tickets.

• Success Plans.

• Business Reviews.

Every customer conversation. Every decision. Every challenge. Every outcome.

And being able to instantly understand the customer's journey from the moment they first engaged with your company.

That would completely change how we prepare for executive conversations and maintain continuity when stakeholders change.

Yesterday, I did a fun experiment, and it blew my mind.

I provided AI 18 call transcripts from the most recent implementation of one of my customers and asked it to give me a summary of:

• Key stakeholders, their roles, and responsibilities

• Business outcomes, current challenges

• Any metrics that were brought up during the calls

This has been the most detailed Implementation-to-CS transition document I’ve seen in my life. I can literally build my initial Success Plan with that briefing.

Rebuilding my data analysis workflows

Anyone who has worked in Customer Success knows how much time disappears inside spreadsheets.

• Exporting data

• Cleaning reports

• Combining datasets

• Pivot tables

• Looking for trends

• Building recommendations

This is probably the area where I spend the most time today.

I'm excited to explore how tools like Claude Code can automate portions of that work so I can spend more time helping customers take action and less time preparing the analysis itself.

Will all of these ideas work?

Probably not.

Some of them may fail completely.

Others may require dozens of attempts before they deliver the results I'm looking for.

But one lesson I took away from the Summit is that progress doesn't come from waiting until you know exactly how to build something.

It comes from being willing to start.

To test.

To iterate.

To get stuck.

And then use AI to get unstuck.

The presenters at the Summit weren't successful because they knew exactly what to build. They were successful because they were willing to keep iterating until they figured it out.

That's the mindset I'm taking with me.

More learning.

More experimentation.

More building.

Because every hour I invest in learning how to use AI more effectively is an hour I can give back to my customers through better insights, better preparation, and better outcomes.

And if it takes 1,000 iterations to create something that helps me deliver more value to my customers, it'll be worth every one of them.

I'd love to hear from you.

What are you currently building with AI? Hit reply and let me know ☺️

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

It's here.

The Success Plan Playbook is officially live — and I couldn't be more excited (or relieved) to finally put this in your hands.

And honestly? This one means a lot to me. I have been working on this playbook for the past 2 years, and I can’t believe it is ready to be shared!

But before I tell you what's inside, I want to tell you why I built it.

Here’s the story.

Why I wrote The Success Plan Playbook

2.5 years ago, I was promoted to Strategic CSM at my company. One of my main goals was to build more strategic Success Plans for my Enterprise accounts.

So I did what you would have done in my position:

1. I searched for anything online that could help me build better plans

2. I watched as many webinars on Success Plans as I could find

3. I tried to reverse-engineer every example I could find online

And after all of that? I had a folder full of templates. Beautiful ones, actually.

But not a single resource walked me through the thinking behind the plan.

• How do you decide what outcomes actually matter to an executive?

• How do you connect a product feature to a financial result?

• How do you build something an executive looks at and says — “yes, this person gets it!”

And while the templates were helpful, they weren’t enough.

What I needed was someone to walk me through the full strategic thinking process.

Not just what goes into a success plan, but how to actually build one that feels strategic, credible, executive-facing, and tied to real business outcomes.

So I built that system myself.

Through trial, error, and a lot of iteration. And once I had it — once I could see the framework clearly — I realized I had to share it.

Every time I talked about success plans on LinkedIn, my inbox filled up with the same questions:

• "How do you actually make them strategic?" 

• "How do you get executives to care?" 

• "How do you tie this to revenue?"

• “How do you build one when the customer doesn’t even know what success looks like?”

Most CSMs know they need a success plan. Very few know how to build one that executives respect.

That gap?

It's the difference between being seen as a vendor and being seen as a strategic partner.

So I built the system I wish I had.

What’s inside

The Success Plan Playbook is a 7-step, end-to-end framework for building Success Plans that tie directly to business outcomes — the kind executives actually care about.

Here's what I walk you through:

• The ICE Research Framework — how to deeply understand your customer's industry, company priorities, and executive agenda

• How to extract strategic insights from a 10-K report so you can speak your customer's language at the board level

• How to run discovery that builds authority — not just a checklist, but a conversation that positions you as a thought partner

• How to assess product usage and identify alignment gaps between what your customer is doing and what they need to achieve

• How to define and measure business outcomes that go beyond product adoption and tie directly to financial results

• How to build milestones tied to accountability so the plan doesn't die after the first call

• How to turn a success plan into a living strategy — something that evolves with your customer and keeps you at the center of their growth

The exact playbook I use to manage my strategic portfolio today. I call it the Success Planning OS.

This playbook is for you if…

• You want to get out of reactive mode and lead strategically

• You manage (or want to manage) enterprise or high-value accounts

• You're tired of theory and want a proven, repeatable system

• You want to earn a seat at the table with executives

• You need a roadmap to align customer goals, outcomes, and impact

• You're ready to drive renewals, expansions, and revenue — on purpose

Ready to get started?

👉 Grab your copy of The Success Plan Playbook here

I'll be sharing more over the coming weeks — including a few free frameworks pulled directly from inside the guide. So even if you're not ready to dive in yet, stay close.

There's a lot more coming.

Thank you for being here. This community is why I keep building.

Let's get strategic.

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

Three years ago, I inherited an account that was at risk.

They had a ton of product feedback, open challenges, and a long list of things they needed from our solution that we didn't have at the time.

But here's the interesting part...

This was also one of the most engaged customers I had ever worked with.

They showed up prepared. They shared detailed feedback. They knew exactly what was working, what wasn't, and what they needed to make the product more valuable for their business.

And honestly?

That kind of customer is a gift. A challenging gift, but still a gift.

Because when customers are willing to tell you exactly where the gaps are, you have an opportunity to do something with that information.

The account had a lot going on. Senior stakeholders changed roles. New leaders came in with higher expectations. Some were demanding. Some were highly technical. And none of them were afraid to tell me when we were falling short.

At the time, the account was around $200K in ARR. And I knew that if we wanted to retain it, let alone grow it, I had to do more than listen and say, "Thank you for your feedback."

I had to take action.

So I partnered very closely with Product.

Their feedback made complete sense. They were asking for capabilities we didn't have, but these were not random requests. They were asking for features that would deliver real operational value — features that would help them work better, improve day-to-day operations, and if built, benefit many other customers too.

So I did what I do best. I built the business case.

I documented the needs clearly. I explained what the customer was trying to accomplish, why these capabilities mattered, and the impact the gaps were having on their operations.

And most importantly, I positioned their feedback in a way that made sense for Product, Engineering, and leadership.

Because this is something I've learned over the years: customer feedback is only powerful when you translate it correctly.

It's not enough to say, "The customer wants this feature."

You have to explain:

• What business problem are they trying to solve?

• How many users are impacted?

• What happens if we don't address this?

• Could this benefit other customers?

• Is this tied to retention, expansion, or strategic value?

That is where CSMs can have a massive impact. We are the bridge between what customers experience and what internal teams need to understand.

So I worked closely with Product to shape the stories. I gathered context, provided examples, and followed up every week. I kept the customer informed and internal teams aligned. And I made sure their feedback didn't get lost in a backlog somewhere.

Over time, about 90% of their asks were addressed — and these improvements strengthened the product for more than just this one account.

That's when the relationship started to shift.

The customer could see we were listening. They could see we were taking their feedback seriously. And they could see I wasn't just showing up to manage the account — I was advocating for them. I was helping them get closer to the outcomes they cared about.

Slowly, trust started to build.

The account grew. They doubled their licenses. I took this account from $200K to $450K in ARR — $250K in growth from an account that started as a risk.

But I want to be clear: this did not happen overnight.

It took time, patience, and a lot of hard work. It took multi-threading the account and building relationships across IT, Product, Real Estate, and Security. It took cross-functional collaboration, because CSMs cannot protect and grow accounts alone. We need Product, Engineering, Support, Sales, and leadership. Everyone plays a role in customer retention.

Today, this customer continues to be one of my most engaged accounts. They still share challenges. They still have high expectations. But they trust me — not because everything was perfect, but because when things were difficult, I showed up. I listened, took action, engaged the right teams, and made sure they felt heard.

Right now, this same customer is exploring two additional products from our suite, which could represent another $200K in ARR.

That is the power of turning feedback into action.

At-risk accounts are not always lost accounts. Sometimes they are the accounts with the biggest potential — but only if you're willing to lean in, understand the real business problem behind the feedback, and partner internally to solve it.

Our job as CSMs isn't just to collect feedback. It's to translate feedback into business impact, protect revenue, and when the opportunity is there, grow it.

Have you ever worked closely with Product to protect an account or turn around a customer relationship? Hit reply and share your story.

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

In 2020, I made a decision that changed my career.

I stepped back from my leadership role and went all in on Customer Success.

Four years later, I moved from entry-level CSM to Strategic CSM, managing global enterprise accounts.

It wasn’t luck.
It wasn’t timing.
And it definitely wasn’t waiting around for someone to hand me a bigger title.

It was intentional.

Here are the 15 things I did differently.

If you’re an early-career CSM and want to move into enterprise, this is your roadmap.

1. I invested in myself

I read every Customer Success book I could get my hands on.

A few that shaped me:

• The Outcome Generation – Paul Henderson

• Selling to the C-Suite – Nicholas A.C. Read & Stephen J. Bistritz

• The Customer Success Professional’s Handbook – Ashvin Vaidyanathan & Ruben Rabago

• The Chief Customer Officer Playbook – Jeanne Bliss

• Doing Discovery – Peter Cohan

• The Seven Pillars of Customer Success – Wayne McCulloch

• Chief Customer Officer 2.0 – Jeanne Bliss

• The Chief Customer Officer Playbook - Rod Cherkas

• REACH – Rod Cherkas

• Never Split the Difference – Chris Voss (with Tahl Raz)

• The Strategic Customer Success Manager – Chad Horenfeldt

I absorbed as much knowledge as I could in a very short period of time.

Every book changed how I show up with my customers and got me closer to where I am today.

2. I listened to the best

Podcasts during workouts.
CS webinars at night.
Industry panels on weekends.
I attended CS conferences and events.

I studied how strong CSMs ask questions.
How they position value.
How they think about revenue.

I stopped consuming random content.
I consumed strategically.

3. I tracked my numbers obsessively

This is where things shifted.

I stopped saying “my accounts are doing well.”

Instead, I tracked:

• GRR

• NRR

• Expansion rate

• Adoption trends

• Product usage

• YoY growth

• Risk indicators

At one point, I closed a year at 136% NRR.

Strategic CSMs think in numbers.
If you don’t know your metrics, you can’t lead.

If you want to learn more about how to track your metrics, this YouTube video is for you.

4. I learned to read and analyze 10-K reports

Most CSMs never open a 10-K.

I started downloading them before every executive conversation.

I looked for:

• Cost reduction initiatives

• Lease liabilities

• Strategic risks

• Executive commentary

• Investment priorities

When you quote their annual report back to them, the conversation changes.
You start sounding like a business partner.

5. I built frameworks where none existed

I’m not naturally organized.

So, I built systems.

• Research frameworks (Industry, Company, Executive)

• Discovery templates

• Success Plan structure

• Milestone trackers

• Health score models

• AI prompts for research

Strategic work depends on structure. 

6. I surrounded myself with people smarter than me

I joined Slack groups.
I engaged in CS communities.
I built relationships on LinkedIn.

I asked questions publicly.

I shared ideas and put myself out there.

I learned from operators who were way ahead of me.

Your environment matters more than you think.

How’s that saying go?

“You are the average of the five people you spend the most time with.” — Jim Rohn

7. I shared my journey online

I started writing consistently.

No big audience.
No polished strategy.

Just lessons I was learning in real time.

That grew to 19,000+ followers on LinkedIn.
And +2,500 subscribers on this newsletter. (Thank you for being here)

Building in public did four things:

1. It forced clarity.

2. It forced me to level up.

3. It built authority before the title caught up

4. And… it landed my first Enterprise CSM role 5 years ago.

8. I invested outside of my job description

I built:

• Internal coaching sessions

• Onboarding resources

• EBR Templates

• Success Plan Playbooks

• Internal processes

• CS training decks

• AI initiatives

No one asked me to.

I saw gaps and filled them.

That’s how leaders are built.

9. I embraced revenue ownership

I stopped thinking:

“I manage accounts.”

I started thinking:

“I own a business portfolio.”

That changed how I approached:

• Renewals

• Expansion timing

• Risk mitigation

• Executive engagement

Revenue is not only a Sales problem.

If you want to manage enterprise accounts (especially in 2026), you need a revenue-driven mindset.

10. I learned cross-functional influence

Instead of escalating product issues emotionally, I translated them into ARR impact.

Instead of saying “this feature is broken,” I said:

“This impacts $X in expansion potential or retention.”

Product (and leadership) listens when you speak in business terms.

11. I did the role I didn’t have yet

This one matters.

Before I ever managed enterprise accounts, I started treating my existing customers like enterprise customers.

I researched their industry.
I mapped stakeholders.
I documented goals.
I tried to understand how their teams were measured.

The habits I built became the foundation for managing global enterprise accounts.

Strategy is a muscle.

You build it long before you actually need it.

12. I got comfortable with executives

I stopped fearing C-level titles.

CIO.
VP.

They are measured on KPIs like everyone else.

When you understand what they are measured on, conversations become easier.

Executives don’t want feature updates.

They want clarity, context, and direction.

13. I adopted AI early

I bought my ChatGPT premium subscription the day it was available and long before Copilot was adopted in my company.

I used AI to:

• Summarize 10-Ks

• Prepare executive questions

• Research industries

• Draft milestone plans

• Refine value messaging

• Better communicate ROI

Strategic CSMs move faster by using tools well.

AI won’t replace strategy.

But it will replace tactical work.

14. I narrowed my focus

When I moved from hundreds of accounts to Enterprise, I used the space wisely.

I went deeper.

• More research

• Better documentation

• Stronger executive relationships

• Clearer success plans

Depth creates authority.

15. I documented everything I learned

Early in my career, I realized something.

Every problem I solved…
Every discovery call that went well…
Every mistake I made…

There was a lesson in it.

So I started documenting everything.

Frameworks.
Strategies that worked.
Lessons from churn.

Over time, those learnings turned into templates.
Then playbooks.
Then training sessions.

Eventually, they became the foundation for the resources and content I share with you today.

Growth compounds when you capture what you learn.

What changed?

I didn’t wait to be promoted.

I started operating at the next level.

That’s the difference.

If you’re feeling stuck, here’s what I want you to remember:

Being busy is not the same as being strategic.

Strategy is built intentionally.

And it’s learnable.

You don’t need 10 years of experience.

You need:

• Curiosity

• Systems

• Executive awareness

• Revenue mindset

• Consistency

That’s how I went from entry-level CSM to Strategic CSM in four years.

And if you’re willing to do the work, you can do it faster.

Are you looking to get promoted? What’s the one skill you know you need to work on next?

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

When it comes to learning more about Enterprise customers, most CSMs stick to the same playbook:

• Review Sales to CS handoffs
• Review CRM notes
• Ask discovery questions
• Track product usage
• Analyze support tickets

These are important… but they only tell part of the story.

What if there was another way to get deeper insight?

One that reveals true business priorities, uncovers cost-saving initiatives, and shows you exactly what matters at the executive level?

It’s often overlooked.

The company’s 10-K report.

But first… what is a 10-K report?

A 10-K is the annual report public companies file with the SEC (Securities and Exchange Commission).

It includes:

• Business overview
• Financial performance
• Cost reduction initiatives
• Strategic priorities
• Risk factors
• Executive commentary

In other words…

It’s the closest thing you’ll get to sitting in their boardroom.

And if your stakeholder is a VP or C-level leader, this is what shapes their agenda.

Let’s break it down.

How to use a 10-K report

You don’t need to be a finance expert.

You just need a simple process.

Step 1: Download the latest 10-K

Go to your customer’s Investor Relations page.

Look for:

• “Investor Relations”
• “Financials”
• “SEC Filings”

Download the most recent 10-K (by year).

💡 Pro-tip: Always use the latest version—priorities change.

Step 2: Familiarize yourself with one report

The first time I opened a 10-K, I didn’t analyze it.

I browsed it.

I wanted to understand what information was included and what could actually help in my day-to-day conversations.

That first pass made everything easier.

It helped me recognize patterns, identify key sections faster, and know what to look for next time.

As you scan, look for themes relevant to your industry.

In the workplace space, I consistently found:

• Real estate portfolios (size, footprint, locations)

• Lease information (owned vs. leased)

• Cost reduction initiatives

• Hybrid work strategies

• Operational efficiency efforts

Once you’ve done this once or twice, you stop reading…

You start scanning with intent.

Now that I understood what to look for, I optimized my approach using AI.

Step 3: Use AI to summarize the report

10-Ks are long. You don’t need to read them cover to cover.

Use AI to extract what matters.

Here’s the prompt I use:

This gives you a clear snapshot of priorities, risks, and goals—straight from executive leadership.

If needed, follow up with:

• What are the top strategic initiatives this year?

• Are there mentions of cost reduction or consolidation?

• What risks are most emphasized?

💡 Pro-tip: Always validate key insights. That’s why I ask for page references.

Step 4: Validate and dig deeper

Go back into the report and search for specific terms.

My go-to keywords:

• “real estate” / “office space” / “portfolio”

• “consolidation”

• “lease liabilities” / “operating costs”

• “cost optimization”

• “hybrid work” / “remote”

• “efficiency” / “streamline”

These point directly to strategic priorities and cost pressures.

Adjust based on your industry.

Here’s what this looks like in practice

Last year, I inherited an enterprise account with no documented goals, no clear challenges, and zero executive context.

And I had a call scheduled with the VP, Global Real Estate.

I didn’t want to show up asking vague questions or waiting for direction.

I wanted to lead.

So I pulled their 10-K.

Here’s what I found:

1. Strategic Goal: Footprint optimization

“ACME has continued efforts to optimize its real estate footprint… including consolidating office space and renegotiating leases.”

“ACME highlights its intention to operate more efficiently as a lean, agile company.”

2. Financial signal: Lease Liabilities Decreasing

Lease liabilities dropped 9% YoY.

A clear signal they were actively reducing real estate spend.

2024, 10-K Report (ACME company)

3. Operational Focus: Hybrid Enablement

The report outlined how hybrid work would shape operations and drive investment in workplace technology.

———-

Armed with this, I walked into the meeting prepared.

Instead of asking:

“What are your current goals?”

I led with:

“I reviewed your 10-K and saw a strong focus on real estate consolidation. Based on your current setup, there’s an opportunity to unify workplace data and improve visibility into space utilization. I’d love to explore that with you.”

The tone shifted instantly.

The VP leaned in.

We skipped surface-level conversation and went straight into strategy.

That one insight built immediate credibility.

Why this works

Executives don’t care about features.

They care about business problems.

When you show up already understanding their priorities—with data to back it up—you:

• Build executive trust
• Shift from tactical to strategic conversations
• Align your product to measurable outcomes
• Create momentum for renewals and expansion

You’re no longer just checking in.

You’re helping them hit board-level goals.

Your 3-step challenge

Pick one of your enterprise customers (public company) and:

1. Download their latest 10-K

2. Run the AI prompt + validate insights

3. Identify one priority and connect it to your product

Bring that into your next call.

Watch how the conversation changes.

P.S. If you try this, let me know how it goes!

This is part of a bigger system

What I shared here is one piece of how I approach Success Planning today.

It’s part of a broader framework I use to understand my customers, align with executive priorities, and build plans that drive real business outcomes.

The Success Plan Playbook - Coming soon 🔜

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

There are no shortcuts to executive conversations.

If you want to be seen as a strategic partner, you have to do the work.

One of the best books I’ve read on this is Selling to the C-Suite. There’s a quote that stuck with me:

Let that sink in.

Before you meet them.

Not during the call.
Not after discovery.
Before.

Because from their perspective, everything you need is already out there:

• Their company’s strategy

• Their industry challenges

• Their priorities

• Their pressure

They don’t have time to walk you through it.

And if you show up asking questions you could have answered yourself… you lose credibility before the conversation even starts.

Another line from the book says it even more directly:

That’s the job.

The difference between a reactive CSM and a strategic one is simple:

One shows up with questions (“What’s keeping you up at night?”- Sound familiar?)
The other shows up with context.

So let’s talk about how to do that digging.

Let’s assume the executive stakeholder is a VP, Global Real Estate.

1. Start with LinkedIn (but go deeper than most)

Most CSMs glance at a profile. Strategic CSMs study it.

Look for:

• Time in their role

• Previous experience

• Recent promotions

• Posts or articles shared

• Language they use repeatedly

If your executive keeps talking about “cost optimization” or “efficiency,” that’s your signal.

That’s the language you should be using in your next conversation.

2. Use AI to understand their role in minutes

You don’t need to guess what your executive cares about.

Use AI to study their role.

Prompt example:

“What KPIs is a VP of Global Real Estate typically measured on in a Fortune 500 financial services company?”

In 30 seconds, you’ll get:

• Cost per seat

• Total occupancy cost

• Portfolio optimization

• Space utilization

And their number 1 priority?

Now you understand how they are measured.

If you don’t know the scoreboard, you can’t connect your product to value.

(And remember: validate what AI gives you. It’s a starting point, not the answer.)

3. Search for conferences, interviews, and panels

Google their name plus:

• Conference

• Keynote

• Interview

• Podcast

Executives often say publicly what they won’t repeat in a 30-minute call.

While researching one of my executive stakeholders (VP, Global Real Estate), I found a conference where he was speaking.

The topic?

“Business-driven technology strategy for a shifting corporate Real Estate and Facilities market.”

That told me everything.

How he was thinking about automation, technology strategy, and innovation across a global portfolio.

So I prepared differently.

Instead of asking, “How is everything going?” I said:

“I saw your session on business-driven technology strategy. You mentioned automation and better portfolio visibility. Are you confident in the data guiding your consolidation decisions today?”

The tone shifted immediately, and this opened up a discussion on one of the most pressing challenges he was facing: measuring actual utilization, not just booking utilization. This eventually led to a solution that allowed us to measure badge swipes to improve occupancy accuracy - a key metric that helps guide decisions for portfolio optimization.

When you listen to how executives speak externally, you gain their language, their focus, and their level of ambition.

That’s how you prepare at an executive level.

4. Read similar job descriptions

Google search or go to any job site (Ej. Linkedin, Indeed, Glassdoor, ZipRecruiter).

Search for roles with the same title.

Why this matters?

Job descriptions list responsibilities, metrics, and current initiatives.

If multiple roles mention:

“Drive portfolio optimization and site planning to improve efficiency, reduce costs, and support growth.”

This tells you analytics and visibility are strategic priorities.

If your product produces utilization dashboards and reporting, now you have a direct bridge to business outcomes.

5. Review public financial reports (if applicable)

If your customer is public, read their 10-K report.

You don’t need to read every page. Use AI to summarize the most relevant sections tied to how your product can help that executive.

For my industry (workplace), I look at:

• Cost reduction initiatives

• Real estate footprint

• Operating leases and costs

• Operational efficiency

• Risk factors

• Strategic initiatives

• Hybrid work initiatives

When I did this for a financial services customer, I uncovered:

• 7% reduction in square footage year over year

• $81M decrease in lease liabilities

• Clear hybrid work positioning

Imagine walking into a meeting and saying:

“I noticed lease liabilities decreased by $81M since 2022. What data is driving your decisions around which leases to renegotiate or exit next?”

That signals preparation and business acumen.

6. Tie everything back to your product

Research alone doesn’t make you strategic.
Translation does.

Instead of saying:
“Adoption is low.”

You say:
“If we increase adoption from 20% to 70%, we can improve visibility into space utilization and support your cost reduction goals.”

That’s the shift:
Feature → Behavior → Data → Business impact.

How to prepare like a pro

Before every executive meeting, ask yourself:

• Do I know how this person is measured?

• Do I understand their top 2–3 strategic priorities?

• Can I clearly connect my product to those priorities?

• Am I bringing one relevant insight to the conversation?

If the answer is no, pause and prepare.

Executives don’t need more status updates.
They need clarity, context, and direction.

Research is not extra work. It is part of the job.

And if you want the full ICE research framework (Industry, Company, and Executive Stakeholder) plus AI prompts and templates, it’s all part of the Success Plan Playbook (Coming soon!)

If building stronger executive relationships is one of your goals this year, this is your starting point.

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

It took me a while to fully understand this.

Customer Success is not about adoption.
It’s not even about keeping your customers happy.

It’s about ROI.

If your customer cannot clearly see the return they are getting from their investment, everything else becomes noise.

Let’s break this down in a practical way.

What is ROI?

ROI stands for Return on Investment.

In simple terms, it answers one question:

Was this investment worth it?

In business, ROI measures the return of an investment relative to its cost. It is usually expressed as a percentage.

The formula is straightforward:

ROI = (Net Profit / Cost of Investment) x 100

Where:

Net Profit = Total Gain from the investment – Total Cost of the investment

That’s it.

Executives use this logic every single day. Whether they are buying software, hiring headcount, opening a new office, or launching a new initiative, they are asking:

• What will we gain?

• What will it cost?

• Does the math make sense?

If the answer is yes, they move forward.

If the answer is unclear, they hesitate.

If the answer is no, they cut it.

A simple example (from my personal life)

I used to spend 2 hours per week manually tracking expenses in spreadsheets.

Logging into my multiple bank accounts.
Classifying every type of expense into a spreadsheet.
Creating formulas to track income and spending.

It worked.

But it was time-consuming.

2 hours per week x 52 weeks = 104 hours per year

If my time is worth $75 per hour, that is:

104 hours x $75 = $7,800 per year.

That’s what my “free” spreadsheet system was actually costing me.

Then I switched to a budgeting tool (YNAB) that costs $191 per year. 

It connects to my bank accounts automatically.
Transactions are categorized for me.
The reports are built in.

What used to take two hours now takes a few minutes.

Now let’s look at the math.

Net profit:

$7,800 – $191 = $7,609.

ROI:

$7,609 / $191 x 100 = 3,983%

When you look at it that way, the decision becomes obvious.

I’m not paying $191 for a tool.

I’m investing $191 to recover $7,609 worth of time and mental energy.

That is an obvious investment.

Businesses think the exact same way.

Just with a lot more zeros!

What ROI means in Customer Success

Customers do not buy software for features.

They buy it because they believe the investment will:

• Increase revenue

• Reduce costs

• Improve productivity

• Reduce risk

In other words:

It makes financial sense.

Your job as a CSM is to make that financial sense visible.

Not assumed.
Not implied.
Visible.

For example, in the workplace technology industry that I work in, ROI might look like:

• Reducing real estate footprint

• Increasing space utilization

• Lowering cost per seat

• Eliminating manual reporting (productivity, time saved)

In the MarTech space, it might look like:

• Increasing pipeline

• Improving conversion rates

• Reducing customer acquisition cost

Different industries. Same principle.

ROI is the bridge between product usage and executive value.

How to calculate ROI in your accounts

You do not need a finance degree to do this.

You need clarity.

Start with three simple questions:

1. What was the customer doing before?

2. What changed after implementing your product?

3. What is the financial impact of that change?

Let’s use a workplace example.

Before:

• 15,000 square feet

• 20% utilization

• $345 per square foot

• Total annual cost: $5.1M

After optimization:

• 7,000 square feet

• 60% utilization

• Same cost per square foot

• Total annual cost: $2.4M

Net savings:
$5.1M – $2.4M = $2.7M

Now imagine your software costs $300,000 per year.

ROI:
$2.7M / $300,000 x 100 = 900%

That changes the conversation.

Now you are no longer discussing “feature adoption.”

You are discussing $2.7M in savings.

Why this matters to you

Last week, I asked you where you are in your CS journey.

43% of you said you are already managing enterprise or strategic accounts.

At that level, ROI is not just helpful.

It is expected.

Enterprise customers operate under constant scrutiny.
Budgets are reviewed.
Procurement gets involved.
Every line item is questioned.

And when renewal season comes around, the conversation becomes very simple:

“What did we actually get from this investment?”

This is where many CSMs struggle.

They show:

• Adoption charts

• Feature usage

• Training sessions delivered

• Support tickets resolved

But none of those answer the question executives actually care about.

What was the business impact?

When you can quantify ROI:

You defend renewals.
You create expansion opportunities.
You earn executive credibility.

And most importantly, you shift the conversation away from price and toward value.

Executives do not renew contracts because users like the interface or because they are logging in.

They renew because the investment makes financial sense.

Period.

ROI is not just about savings

Sometimes ROI is about:

• Avoided risk

• Improved compliance

• Faster decision-making

• Increased employee satisfaction tied to retention

Not everything fits neatly into a spreadsheet. But even qualitative impact should connect back to business results.

A useful question to ask yourself is this:

“If this product disappeared tomorrow, what financial or operational gap would it create?”

If the answer is unclear, there is probably more work to do.

Final thought

ROI is not just a financial metric.

It is a credibility metric.

When you can translate product outcomes into financial outcomes, you change how you are perceived.

You stop being the person who manages accounts.

You become the person who drives business impact.

And in a world where roles are evolving, and AI can automate tactical work, strategy and financial fluency are not optional skills.

They are your edge.

If you want to go deeper into how to define outcomes, tie them to measurable metrics, and build Success Plans that make ROI obvious, that is exactly why I wrote the Success Plan Playbook (coming soon!)

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

It’s been more than six months since my last newsletter.

That wasn’t the plan.

If you’ve been here for a while, you know I care about consistency. But 2025 stretched me in ways I didn’t expect. Instead of sending something rushed, I stepped back and focused.

For those of you who joined recently, let me reintroduce myself.

I’m Erika. 👋🏻
Strategic CSM. Enterprise, global accounts. Revenue ownership.
Obsessed with becoming the most strategic, high-impact CSM I can be.

And for those who’ve been here a while — thank you.

I stepped away for a reason.

Over the past two years, I’ve been building something that demanded far more time and energy than I expected: The Success Plan Playbook.

It’s the most strategic work I’ve created so far. And it required my full attention.

But the bigger reason I’ve been thinking differently isn’t just the playbook.

It’s what I’ve seen happening around me.

The CSM role has changed

The post-sales environment for SaaS shifted toward higher scrutiny and tougher retention math: tech layoffs stayed elevated, budgets tightened, procurement influence increased, and expansion became harder.

I’ve seen this firsthand in my own business portfolio.

• My customers experienced layoffs.

• The champions I built relationships with? Gone.

• Executive stakeholders changed.

• Budgets froze.

• Procurement analyzed every subscription line with a microscope.

• Executives demanded more.

And I felt the pressure.

Not just to manage my accounts.
To defend them.

And layered on top of all of this — AI.

I follow earnings calls. I read what CEOs are saying.

Last week, Block (Fintech company) announced it was laying off roughly 40% of its workforce — around 4,000 people — as it leans further into automation and AI-led efficiency.

And I’m seeing this all around.

Companies are no longer asking, “Should we experiment with AI?”

They’re asking, “How can we use AI to operate leaner?”

And when that question gets asked, every function is examined.

Including Customer Success.

If reporting can be automated, it will be.
If onboarding flows can be standardized, they will be.
If risk alerts can be surfaced automatically, they will be.
If decks can be generated from usage data, they will be.

So the real question becomes:

What remains uniquely human?

Judgment.
Context.
Influence.
Strategy.

AI can surface churn risk.
It cannot defend a budget in front of a CFO.

AI can show usage trends.
It cannot navigate stakeholder politics mid-renewal.

AI can optimize the renewal process.
It cannot earn executive trust.

When execution becomes automated, value concentrates in IMPACT.

That forced me to rethink how I show up in my role.

What this means for you

If you’re in Customer Success right now, the bar is rising.

Tactical work is easier than ever to replace.

What’s harder to replace?

• Thinking in business outcomes.

• Influencing executive decisions.

• Connecting usage to revenue, cost savings, or risk reduction.

• Anticipating renewal risk months before it surfaces.

• Aligning stakeholders around measurable value.

That’s strategy.

It protects your role.
It expands your influence.
It moves you from vendor to revenue partner.

Being strategic doesn’t mean doing more.

It means understanding how your customer makes money.
Knowing how your executive is measured.
Framing every recommendation around impact.

The CSMs who operate at this level become indispensable.

And that’s what the next chapter of this newsletter will focus on.

Where this newsletter is going

Over the past five years, I’ve documented my journey as a CSM. As I’ve evolved, so has my content.

This space won’t be about generic CS advice.

It will be about how to think, operate, and show up like a Strategic CSM in an environment where “good enough” is no longer safe.

Six months from now, if you’re reading consistently:

• You’ll build real business acumen.

• You’ll prepare for executive meetings differently.

• You’ll ask sharper discovery questions.

• You’ll tie your product to financial outcomes naturally.

• You’ll protect renewals before they’re at risk.

• You’ll own revenue.

That’s the shift.

One thing you can use today

Before your next customer call, ask yourself:

Do I know how this stakeholder is measured this year?

If you don’t know their KPIs, you’re not operating strategically yet.

Start there.

It will change how you listen, what you say, and what you recommend.

One quick question

Before I shape the next few issues, I want to understand who’s here.

I’m so excited for the next chapter of this newsletter.

Thanks for being here!

Best,
Erika

Erika Villarreal

Hi {{ first name | there }},

“You need to be more strategic.”

If you’re a CSM, you’ve probably heard this from your manager before. But what does “being more strategic” actually mean? How do you do it when your day is packed with customer escalations, QBRs, and a million little tasks that feel important?

For years, many CSMs have fallen into the trap of being everything to everyone: acting as support, project managers, coordinators, and escalation points all at once. We’ve been conditioned to jump on every request, fix every problem ourselves, and spend our days reacting instead of consulting. In many ways, we have been trained to be professional firefighters, juggling tactical tasks all day long to keep the churn monster at bay.

Economic pressures, tighter budgets, and rising expectations are forcing companies to rethink what they need from Customer Success. Leaders are realizing that reactive customer management doesn’t cut it. If we want to keep customers, grow accounts, and help our companies thrive, we have to show up differently.

Enter: The Strategic CSM.

In his book The Strategic CSM, Chad Horenfeldt sums it up perfectly:

“The old CSM playbook isn’t good enough anymore. CSMs and CS leaders need to take a different approach if they want to maintain or improve renewal rates and uncover revenue opportunities.”

What is a Strategic CSM?

A Strategic CSM isn’t just a title; it’s a mindset shift.

Think of it like this:

A Strategic CSM goes beyond their basic responsibilities of driving product adoption and dives deeper into the customer’s business. They focus on truly understanding how their customers’ company operates: their goals, challenges, market pressures, and what matters most to executive stakeholders.

They spend less time talking about features and more time connecting the dots between their solution and the customer’s broader business outcomes. They ask the hard questions, challenge assumptions, and proactively uncover obstacles before they become roadblocks.

In other words, Strategic CSMs make it all about the customer. Not their company, not their product. They become trusted advisors who guide customers toward results they might not reach on their own.

As Chad writes:

“Strategic CSMs lead with insight, ask better questions, and drive measurable outcomes.”

Characteristics of a Strategic CSM

So what makes a Strategic CSM stand out?

• Outcome-oriented: They put the customer’s business objectives above everything else.

• Trust builders: They know trust is the foundation for honest conversations and change.

• Value drivers: They prove the value customers get — they don’t assume it’s obvious.

• Proactive: They spot trends and risks early, not when it’s too late.

• Advisors: They’re not afraid to challenge assumptions or push back (kindly!) when needed.

• Collaborators: They work across Sales, Product, and Support to amplify results.

Most importantly, Strategic CSMs understand they’re not magicians. They know that everyone in the company impacts customer outcomes, and they work internally to ensure their customers’ success.

How to Shift Your Mindset

If you want to become more strategic, start by breaking some old habits.

1. Get out of the weeds, get into the business.
Don’t spend all your time troubleshooting tickets or re-explaining features. Instead, invest that time researching your customer’s industry, reading their earnings reports, and understanding how your product fits into their top priorities. Your goal: know their business almost as well as they do.

2. Ask better questions.
Learn to ask questions that uncover what keeps your customer up at night. I highly recommend listening to this podcast – Beyond Check-in: The questions top CSMs use to build Authority with customers, by Carly Agar.

3. Prioritize building success plans.
Success Plans are the foundation of everything you do. Please don’t treat them as a checkbox; revisit and adjust them as goals evolve. (P.S. The Success Plan Playbook is launching soon, stay tuned!)

4. Build relationships up and across.
If you only know your day-to-day contact, you’re stuck in the weeds. Map out who influences the budget, who defines success, and who could be your champion. Multi-threaded relationships protect renewals and open new doors.

5. Be proactive, always.
Don’t wait for a red flag. Use your data. Are they using the features that help them meet goals? Who’s slipping? Have a plan to get them back on track before they churn.

6. Use your voice inside your company.
Strategic CSMs share customer trends with Product, Sales, and Marketing. Advocate for your customers and back it up with real data and stories

7. Focus your time on what moves the needle.
Audit your week. If too much time goes to support tasks others could own, delegate, automate, or push back. Protect your time for strategic work.

Remember: You don’t have to overhaul everything overnight. Small, intentional shifts add up. Pause every week and ask: “Am I reacting — or driving outcomes?

The Future is Strategic

The rise of the Strategic CSM isn’t just a trend, it’s the evolution of our profession. Our companies need us to be more than product experts. They need us to be business partners, trusted advisors, and connectors of people and outcomes.

If you want the complete playbook to become more strategic in your role, do yourself a favor and grab Chad Horenfeldt’s The Strategic Customer Success Manager book. I can’t recommend it enough.

Onward and upward. ✨

— Erika

Erika Villarreal

Hi {{ first name | there }},

Let’s be honest…

Juggling 30+ accounts as a CSM can feel like frantically spinning plates on sticks.

Each plate is an account in your portfolio. Some are steady and only need a gentle nudge to keep spinning. Some are wobbling dangerously — a renewal at risk, an implementation off track, disengaged stakeholders.

And just when you think you’ve got it under control… another plate appears: a new onboarding, an escalation, a product gap that needs fixing now.

No wonder so many CSMs feel like they’re drowning.

They’re pulled in a hundred directions. Trying to prep for QBRs, chase adoption, rescue renewals, and keep every plate from crashing all at once.

But here’s the truth: Not every plate deserves the same time and energy.

When you know how to prioritize, you stop reacting to every wobble — and start focusing on the plates that matter for your customer and your business.

In this newsletter, I’ll share my PACER-A Prioritization Framework — the simple method I use to score, segment, and focus my attention where it matters most. So you can step off the stage, put down a few plates, and be the strategic advisor your customers need.

Ready?

Let’s do this.

The PACER-A Prioritization Framework

PACER-A stands for:

• Potential

• Adoption

• Churn Risk

• Engagement

• Renewal Timing

• ARR (Annual Recurring Revenue)

It’s a simple scoring method to help you take a messy book of business and rank your accounts, so you always know:

✅ Who needs you now
✅ Who is at risk
✅ Who’s ready for expansion
✅ And who you can confidently deprioritize (for now)

Here’s how to apply it.

Step 1: Profile Your Book of Business

Before you score anything, create a spreadsheet with these data points:

• Potential - How much room is there to expand?

• Adoption - Are they fully using your product? Are there any adoption gaps?

• Churn risk - Health scores, product defects, sentiment – Any signals they might leave?

• Engagement - Are key stakeholders responsive and showing up?

• Renewal - Is it coming up soon?

• ARR - How much revenue is on the line?

This view gives you the data to make smart decisions about where to spend your time.

Step 2: Score your accounts (PACER-A, 0-10 Scale)

Rate each PACER-A dimension on a scale from 0 (Low) to 10 (High).

Here’s how to think about it:

• Potential: High potential for expansion = 8–10

• Adoption: Low adoption = 8–10 (the lower the usage, the bigger the risk)

• Churn Risk: More signs of churn = higher score

• Engagement: Less engagement = higher score (ghosting you is a red flag!)

• Renewal Timing: Renewals in the next 4 months = 8–10

• ARR: The bigger the revenue, the bigger the score (e.g. $500K+ = 9–10)

This helps you instantly see which accounts need your time right now.

Here’s an example, considering today is July 1st:

How to read this:

• Foxtrot Solutions (35) is clearly a top priority: high expansion potential, low adoption, high churn risk, low engagement, plus strong ARR.

• Delta Group (19), Gamma Systems (19), and Helix Partners (18) stand out too — they have high churn risk or near-term renewals.

• Echo Tech (6) is stable — low risk, no renewal pressure, lower ARR — so keep them low-touch.

• Acme Corp (13) and Juno Enterprises (13) show moderate signals — worth attention, but should not be your main focus.

Step 3: Classify into Action Zones

Your total scores now make it easy to split your book into focus areas:

Use this map to build your weekly plan — so you’re not sprinting after every wobbling plate but investing your time where it delivers the greatest impact.

Remember: Priorities can shift quickly. A stable account can show signs of risk overnight. Be prepared to adjust your focus and re-score as needed — that’s how you stay ahead of churn and protect your revenue.

What you learned today

Managing your book of business doesn’t have to feel chaotic.

• Using data gives you a clear, simple view of your portfolio… so you can make better decisions fast.

• A practical scorecard helps visualize your portfolio more clearly.

• Not every customer deserves the same time: focus on where you deliver the biggest impact.

• When you prioritize strategically, you spend less time spinning plates… and more time driving results.

Download the PACER-A scorecard template here.

P.S. I’d love to hear from you. What’s the hardest part of keeping your accounts prioritized right now? Just hit reply and share!

Best,

Erika Villarreal

Hi {{ first name | there }},

Seneca once said, "If a man does not know to which port he's sailing, no wind is favorable."

I learned this the hard way.

Early in my Senior CSM role, I kicked off a large enterprise project with what I thought was a solid Success Plan: enable features, train users, track adoption, run check-ins.

But I never aligned with the executive stakeholder on what success meant to them.

Months later, during our first Business Review, the VP asked:

“How is this helping us reduce costs or improve space utilization?”

And I froze.

Because I didn’t know. My plan was focused on product adoption, not outcomes. I hadn’t defined what success looked like, or who cared most about seeing it.

That moment changed everything for me.

It’s not that I wasn’t working hard… I was. But without a shared goal, my efforts were misaligned. And that’s the issue with most Success Plans:

• They focus on the wrong things

• They miss the bigger picture

• They don’t reach the right people

They don’t fail because we don’t care. They fail because no one taught us how to build them right.

So, if you’ve ever wondered if your plan is actually working… you’re not alone.

Let’s break down the 6 most common reasons Success Plans fail—and how to fix them.

#1 – They Focus on Features, Not Business Outcomes

Success Plans often become checklists: enable integrations, complete training, update settings.

But features aren’t the goal, outcomes are.

❌ “Enable badge integration”
✅ “Gain occupancy insights to support a 10% lease cost reduction by year-end”

🛠 Fix it:
Ask: What business problem does this feature support?
If you can’t answer it, go back to discovery.

#2 – The Goals Are Vague

“Optimize real estate.”
“Improve experience.”
“Drive efficiency.”

These sound strategic, but they’re too broad to track. Without clear goals, it’s impossible to prove progress.

🛠 Fix it:
Turn them into SMART goals:

❌ “Optimize real estate”
✅ “Consolidate 3 floors into 2 by Q3 to reduce lease costs by 15%”

❌ “Drive efficiency”
✅ “Enable badge integration by Q1 and cut manual reporting by 80% by Q2”

Ask: How will we know this is working? If you can’t answer, it’s not ready for the plan.

#3 – They’re Too Tactical, Not Strategic

When your plan sounds like a task list, you’re operating at the wrong level. You’re not hired to list features, you’re there to drive outcomes.

🛠 Fix it:
For every action, link it to a business priority.

Tactical: “Enable badge data integration.”
Strategic: “Provide real-time occupancy data to reduce real estate costs.”

Let your plan show why these tasks matter.

#4 – They’re Shared with Champions, Not Executives

You might create a great plan, but if it never reaches a decision-maker, it won’t influence renewal or expansion.

Champions can support you, but executives drive outcomes and budgets.

🛠 Fix it:
Ask: “Who owns this initiative at the exec level?”
Tailor your plan to them. Strip the feature-speak and focus on ROI, business impact, and strategic milestones.

#5 – They’re Built Too Late

Success Plans aren’t rescue tools, they’re the foundation of everything you do. Waiting until renewal is a mistake. By then, the customer’s perception is already formed.

🛠 Fix it:
Start during onboarding, or even earlier. Use discovery and handoff notes to build a draft. Refine over time.

If you wait until a QBR, you’re reacting. Build early so you can lead the relationship with purpose.

#6 – You Build It Alone

If you build a plan solo and email it for review, don’t be surprised when no one uses it.

When the customer doesn’t contribute, they don’t feel ownership. And if you ignore your internal team, you miss crucial context.

🛠 Fix it:
Build your plan with both your customer and your internal stakeholders.

• Share a draft early and ask: “Does this reflect what you want to achieve?”

• Align with your AE and Sales to stay consistent with commitments

• Involve Implementation, Support, and Exec Sponsors where needed

Success is a team sport. The more voices involved, the more likely your plan will drive results.

What You Learned Today:

Success Plans fail when they:

• Focus on features instead of outcomes

• Rely on vague, unmeasurable goals

• Sound tactical instead of strategic

• Never reach executive decision-makers

• They are built too late

• They are created in isolation

A strong Success Plan isn’t just a document; it’s a shared agreement. A strategic blueprint. A tool to build trust, deliver value, and drive growth.

Coming Soon…

The Success Plan Playbook is almost here.

It’s the guide I wish I had years ago:

✅ A 7-step Success Plan framework
✅ Templates, discovery guides, and AI prompts
✅ Scripts to get executive buy-in
✅ Tools to track progress and prove impact

If you’re tired of guessing your way through planning, this playbook will show you exactly how to do it, step by step.

Want early access? Reply back to this email, let me know what your biggest challenge is when building Success Plans.

P.S. What do you think of the ebook cover? If you clicked, you know.

Best,

Erika Villarreal

Hi {{ first name | there }},

"I’m not in Sales."

If you’re a CSM and this thought has crossed your mind, it’s time for a mindset shift.

The truth is that everyone is in Sales, whether they like it or not.

• Landing your dream job? You sold your skills, your experience, and your potential.

• Going on a date? You sold your personality, values, and charm.

• Negotiating a raise? You sell your value to your company, demonstrating the impact of your contributions.

• Talking to customers? You sell the product, its benefits, and how it solves business challenges.

So, if you’re already doing it daily, why not lean into what you do best—while driving more revenue for your business?

Revenue ownership isn't just a shift in mindset; it's an opportunity to amplify the impact you’re already making. You’re not adding more work—you’re recognizing the value you deliver and using it to drive even greater outcomes.

5 tips embrace a revenue-driven mindset

1. Reframe sales as value exchange

Sales isn’t about pushing products; it’s about showcasing value. In fact, if you’re approach is to bring any solution to your customer just because you need to meet a number, you’re doing it wrong, and this my friend is what will damage the relationship, and how you will immediately lose your customer’s trust.

Every time you help a customer solve a problem, improve efficiency, or achieve a goal, you’re part of a value exchange. Shift your mindset to focus on the outcomes your product delivers rather than the transaction itself.

Think of it this way: when you recommend a great book, movie, or restaurant to a friend, you’re not “selling” in the traditional sense. You’re sharing something valuable because you believe it will enhance their life. Apply this mindset when speaking with customers. It’s about helping, not convincing.

Pro-tip: Create a value proposition matrix highlighting key customer outcomes linked to your product features. Use this to guide conversations and ensure you’re always leading with value.

2. Align Customer Success with business impact

Understand that renewals, expansions, and churn are outcomes influenced by your work. Tie your activities directly to revenue metrics to see the bigger picture.

Everything you do: onboarding, training, driving adoption, and success planning is a revenue driver. When a customer successfully adopts your product, sees value, and stays loyal, that's revenue you helped secure.

Consider the ripple effect: a satisfied customer not only renews but often expands their usage and refers others. This cumulative impact can be substantial over time.

Pro-tip: Implement a revenue impact tracker. Document how your activities contribute to renewals, upsells, and cross-sells. Track metrics like customer health scores, engagement levels, and growth opportunities to make your impact visible. This is an example of how I’ve done this with my own business portfolio.

3. Master the art of discovery

Great salespeople ask the right questions. As a CSM, deepen your discovery skills to uncover customer pain points, growth opportunities, and unmet needs.

Discovery isn’t just for the sales process; it’s an ongoing practice. Regularly engage with your customers to understand how their needs evolve. What worked last year may not be relevant today.

Active listening is key. When you truly hear what your customer is saying (and what they’re not saying), you can tailor your approach to meet their specific goals and challenges.

I recently purchased this book, “Doing Discovery” by Peter E. Cohan. I believe the best CSMs are the ones who can master the art of discovery. I am halfway through the book, and while it is targeted to Sales people, I’ve learned a few tricks to improve my discovery skills. I highly recommend it!

Pro-tip: Develop a discovery question toolkit tailored to your customer segments. Use open-ended questions that encourage customers to share strategic priorities, challenges, and future plans.

Questions like:

• What are your top business goals this year?

• What challenges are you facing in achieving those goals?

• How can we support your growth initiatives?

4. Get comfortable with revenue conversations

Practice makes perfect. Engage in role-plays with peers or mentors to build confidence in discussing renewals, pricing, and expansions.

Revenue conversations don’t have to be uncomfortable. When framed around the value you've provided and the outcomes achieved, they become a natural part of the customer relationship.

The key is to shift from a mindset of “selling” to one of “advising” You’re not asking for something; you’re presenting an opportunity for continued growth and success.

Pro-tip: Role-play scenarios focused on common customer objections. Record and review to identify areas for improvement. Practice transitioning from value discussions to revenue topics smoothly. An example from one of my most recent conversations with a customer:

• Customer: “One of our biggest challenges right now is managing capacity at high demand locations such as Chicago. Users are complaining about not being able to find any bookable spaces, but when they come into the office those desks are free and no-one is sitting there. This is causing pain and friction with the booking process, ultimately impacting end user experience. On top of that, data is not accurate, which is impacting our ability to make decisions with our real estate”.

• Erika: “I understand the pain point. Customers who have faced this issue in the past were able to drastically improve this by implementing our newest feature: an integration between your Access control system (badge RFID) and our booking solution. Users will only be checked-in to their reservations when they badge at the door, if the user did not come into the office that day, the reservation would be automatically released for someone else to book. Customers who have implemented this feature have seen a 50% improvement, while also improving data so you can make better decisions with that space/location.

• Customer: “Great, can you please help me better understand how much this would cost and the effort to implement it?”

5. Embrace a growth mindset

View revenue ownership as an opportunity for personal and professional growth. The more you embrace learning about business acumen and sales strategies, the more impactful you become.

A growth mindset allows you to see challenges as opportunities to learn and improve. Instead of fearing revenue targets, view them as benchmarks for your influence and effectiveness.

Invest in continuous learning. Attend webinars, read industry books, and seek mentorship from colleagues who excel in revenue-related roles. The more you understand the business side of Customer Success, the more confident you’ll feel in owning revenue.

A personal story.

Last year, I did not win CSM of the year, but someone else did.

My approach:

• Report on all the CSQLs this person closed last year.

• Identify the customers that grew in revenue and the industries they belong to.

• Analyze the pain points of those customers.

• Can I identify any of these pain points in the conversations I’m having with my customers?

• How can I use her success to learn and replicate it with my business portfolio?

Pro-tip: Curate a growth library with books, podcasts, and courses on value-based selling, customer success, and business strategy. Recommended resources:

• "The Challenger Sale" by Matthew Dixon and Brent Adamson

• “Doing Discovery” by Peter E. Cohan

• “REACH” by Rod Cherkas

• “How top CSMs nail customer value” Customer Success Career Coach Podcast, Carly Agar.

• From CS to Sales growth: Turning upsells into new sales – Customer Success Pro Podcast, Anika Zubair

The rewards of owning revenue

• Increased earning potential with performance-based incentives. As you contribute to revenue growth, many organizations offer bonuses or commissions tied to your success. This means, of course, more money for you!

• Elevated professional credibility within your organization and industry. Revenue ownership showcases your strategic value, positioning you as a leader in driving business outcomes.

• A seat at the table, influencing not just customer outcomes but business direction. When you impact revenue, your insights become critical in shaping product roadmaps, go-to-market strategies, and growth initiatives.

CSMs, it's time to own your impact. Own the revenue with pride! And I promise you, the rewards will come.

What has been your experience? And how do you feel about this change? Have you embraced owning revenue in your role? I'd love to hear your thoughts!

Best,

Erika Villarreal

Hi {{ first name | there }},

Have you ever struggled to get your customers to see the value of your product? You’re not alone. Many CSMs face challenges when it comes to demonstrating impact and driving adoption. The key to overcoming this? Combining data with storytelling.

Data alone isn't enough. Storytelling alone isn't enough. But together? They're a game-changer.

Most CSMs struggle with driving product adoption and expansion because they focus too much on the features. But customers don’t buy features—they buy outcomes. And the best way to showcase outcomes? Through data-backed storytelling.

Let’s break it down:

• Data gives credibility. It helps you measure the before and after of any change, making it easier to show value.

• Storytelling drives action. Customers connect with relatable success stories more than raw data.

• Together, they influence stakeholders. From adoption to expansion, a compelling narrative supported by numbers makes decisions easier.

Here’s how I use data and storytelling to help my customers achieve their goals:

1. Identify the problem: Look at usage metrics and pain points before implementing a new feature.

2. Craft the narrative: Highlight the challenge, the implemented solution, and the measurable results.

3. Share strategically: Use success stories in business reviews, internal meetings, and customer touchpoints.

The result? Increased trust, better adoption, and more opportunities for expansion.

The process in detail

Step 1: Identify the right data

I have a customer who is always ahead of the curve. They’re my most engaged customer, most successful, and they’re on top of all our new product features, constantly testing new things.

Four months ago, we released a new product feature designed to solve a major challenge: increasing visibility of who is in the office to enhance collaboration and improve data on resource utilization. This feature also aimed to streamline the booking process, making it easier and faster with less friction.

To track the impact, I focused on:

• Desk booking check-in rates

• Desk utilization trends

• Feedback from stakeholders

Step 2: Build a Narrative

Once I gathered the relevant data, I structured the story around the customer’s journey:

• Beginning: Before implementing the feature, the customer faced frequent desk bumping issues due to users forgetting to check-in. This caused inaccurate utilization data and frustrated employees—current metric: 20% desk bumping.

• Middle: The customer implemented the new feature: an integration between our product and their Access Control system, which allowed employees to be automatically checked in to their reservations when they used their badge at the door. This improved the booking experience for the end users and gave them the ability to change their in-office status from working remotely to working at: New York.

• End: Three months after implementing this feature, desk bumping was reduced by 50%, and the accuracy of space utilization data significantly improved, helping the customer make more informed decisions with their space. This also streamlined the booking process, improving the end-user experience, and reducing friction.

Step 3: Presenting the Story

To maximize the impact of this success story, I shared it through various channels:

• Email campaigns: I created an email template to promote this feature with all of my customers who had not implemented this new feature yet. My email focused on the value they would get: 50% reduction in desk bumping, better utilization data, improved user journey.

• Business reviews: I presented the desk bumping trend, which was very similar to my customer’s before implementing the feature: bumping around 20% – 35%, in some cases even higher. I used my successful customer’s result to show how they could bring down this metric, which was key to improving data utilization trends. I highlighted the before-and-after data to demonstrate tangible improvements.

• Customer success touchpoints: I added this topic for discussion in all of my regular cadences, highlighting the benefits once again. I positioned the feature as a strategic enabler for business goals.

Common mistakes to avoid

When combining data and storytelling, avoid these pitfalls:

• Overloading with too much data: Keep it simple and relevant.

• Ignoring the emotional aspect: Data should support the story, not replace it.

• Lack of context: Provide benchmarks and comparisons to give perspective.

If you’re working to get buy-in for new features or driving adoption within your accounts, this approach can help you get there faster.

Resource List

If you're looking to up your CSM game, here are some resources to check out:

• The Power of Storytelling in Customer Success - CS Insider (5 min read)

• Storytelling – Success Coaching (5 min read)

• Using data to drive retention – Erika Villarreal & ClientSuccess (18 min video)

• How to turn data into actionable insights - Elastic (8 min read) – A guide to making data work for you.

• How to leverage usage data to improve product adoption (8 min video) – CSM practice

• Leveraging Product Usage and Adoption Data to Inform Your Customer Lifecycle Engagement - ClientSuccess

Here’s what you learned today:

• Data and storytelling together create a powerful combination to drive adoption and expansion.

• Use before-and-after data to highlight success.

• Share success stories strategically to influence stakeholders.

Tell me—how are you using data to tell success stories today? Hit reply and let me know!

Best,

Erika Villarreal

Hi {{ first name | there }},

Last year in January, I transitioned into a Strategic CSM role—a step up in my career that came with new responsibilities and opportunities to learn and grow in a fast-paced, evolving organization.

For more context, in October 2022, Condeco (my previous company) merged with iOffice and SpaceIQ to create Eptura, the leading WorkTech software solution.

2024 was a year of significant change for my organization, brining with it a set of new new challenges:

📍 Navigating my first merger: I’ve heard stories about what mergers do to an organization, but experiencing it firsthand was entirely different. Eptura’s recent merger brought together nine different products and systems, creating a unique environment of rapid change. While this merger introduced opportunities to align processes and systems, it also brought challenges with accessing complete historical customer information and bridging communication gaps.

📍 Balancing customer needs and learning curves: In my new role, I inherited accounts using products I had never worked with before. Balancing the responsibility of supporting these customers effectively while ramping up on unfamiliar products required a focused, adaptable, and intentional approach to prioritize both learning and delivery.

📍 Building strategic executive relationships: As a Strategic CSM, establishing relationships with executive stakeholders is a critical part of the role. However, many accounts I inherited lacked established executive connections, and my initial contacts were limited to day-to-day product admins. I needed to map out key decision-makers, understand their motivations, and align with their strategic goals.

📍 Driving alignment: Without access to previous success plans or business reviews, I had to start from scratch. Aligning with customer teams on goals, outcomes, and strategic priorities became a key focus to ensure every conversation drove measurable value.

📍 Addressing fragmented data: Accurate data is essential for a Strategic CSM to make informed recommendations. Historical inconsistencies and scattered records required me to proactively bridge gaps, consolidate insights, and build a clear picture of each customer’s current state and goals.

I was thankful that my leadership team recognized these challenges and proactively built strategies to support us. Initiatives like Success Planning enablement, executive sponsorship programs, better data and usage reports, and closer collaboration with Product and Sales teams created a foundation that supported my approach.

I knew that to be successful, I needed to focus on what I could control: learning more about my customers, building stronger relationships, and creating systems to deliver consistent value.

While I am not done yet, I’ve made significant progress.

Here is the plan I put together:

1. Start with a discovery mindset:

To understand my customers better, I embraced curiosity and thorough research. I reviewed contracts and product subscriptions, analyzed historical data (when available), and scheduled discovery sessions to ask open-ended questions about their current priorities and challenges.

I also developed a discovery framework by creating a standardized set of questions to guide initial customer conversations and uncover strategic priorities, gaps, and opportunities. My discovery framework focused on three key areas:

• Company research: Understanding the organization’s priorities and structure.

• Industry trends: Identifying broader market trends that may impact customers.

• Stakeholder goals: Uncovering individual stakeholder motivations and success metrics.

Pro Tip: If historical context is limited, ask customers directly about their workflows, pain points, and success metrics. Their answers will often reveal what’s missing.

2. Learn the products—and their value propositions.

With multiple unfamiliar products in my portfolio, I dedicated time to understanding how each solution worked and the business problems it solved. This remains an ongoing process, and I recognize that deep product knowledge takes time.

I collaborated with internal product experts, attended training sessions, shadowed colleagues, and accessed demo environments to learn hands-on. This practical experience significantly accelerated my learning and gave me the confidence to guide my customers effectively.

Pro Tip: Treat product learning as an ongoing process. Regularly revisit resources and stay updated on feature releases to maintain credibility with customers.

3. Build executive relationships strategically.

I prioritized building connections with decision-makers and executive stakeholders. Using Salesforce, I mapped out existing contacts and identified gaps.

To prepare for strategic conversations, I used ChatGPT and other research tools to better understand executive roles and motivations. For example:

• What is the job description of a VP of Real Estate?

• What are the main responsibilities of a VP of Real Estate?

• Which metrics are most important to a VP of Real Estate?

This research helped me align conversations with their priorities and deliver insights tailored to their goals.

Pro Tip: Executives spend time with CSMs who offer actionable insights that align with their success metrics.

4. Create Success Plans as a baseline for value.

With lessons 1–3 completed, I was ready to draft an initial Success Plan. I partnered with my stakeholders to co-create plans that clarified goals, success metrics, and desired outcomes.

I prioritized my top five accounts, creating detailed roadmaps for collaboration. These plans became central to our ongoing conversations, helping us stay aligned and focused on results.

Additionally, I introduced regular business reviews to communicate progress and adjust plans as needed.

Pro Tip: Introduce the Success Plan early, and use it as a living document to drive ongoing conversations about value and priorities.

5. Proactively address data gaps and inconsistencies.

Data clarity was essential to delivering value effectively. I worked closely with RevOps, Product, and Finance teams to address inconsistencies, consolidate insights, and standardize documentation processes.

To ensure long-term improvements, I built stakeholder maps, gathered product usage data, reviewed contract details, and registered customer goals in our Customer Success platform.

Pro Tip: Approach data inconsistencies with curiosity and persistence. Aligning systems may take time, but it’s worth the effort to create clarity.

Final Thoughts:

This role has stretched me in so many ways, but it’s also been a period of incredible growth. 🚀

Navigating my Strategic CSM role in a post-merger environment reminded me of the power of collaboration, curiosity, and persistence. By focusing on discovery, building relationships, and creating tailored success plans, I’ve been able to have more strategic conversations and deliver lasting value.

The good news?

2025 is already looking brighter. I feel more prepared, focused, and equipped to tackle whatever comes next, with clarity and purpose.

What was your biggest challenge from 2024?
I’d love to hear your thoughts.

Best,
Erika

P.S. I am working on my third guide for CSMs: A Success Plan playbook. In this guide, I will dive deeper into these strategies and offer the step-by-step process to build an impactful Success Plan that drives customer growth 🚀.

Stay tuned for the release.

Erika Villarreal

Hi {{ first name | there }},

We’ve reached the end of 2024, and you know what that means—it’s time to talk CS metrics. This is the perfect moment to reflect on your year, evaluate your performance, and set the stage for 2025.

One of my favorite sayings: “If you cannot measure it, you cannot improve it.”

Your metrics are more than just numbers—they’re your transparent scorecard, a way to spot opportunities or red flags, and the ultimate tool to prove your value to your organization.

Here’s why understanding your metrics is non-negotiable:

1. They boost confidence and credibility. Knowing your numbers positions you as a strategic, data-driven partner.
   

2. They validate your role. Revenue-driven metrics show exactly how you contribute to your company’s success.
   

3. They increase visibility. Impress your manager by owning and interpreting your portfolio's metrics.
   

4. They help identify problems early. Spotting trends allows you to course-correct before challenges escalate.
   

5. They help you land a new role (if you’re looking). Metrics demonstrate your impact in interviews and differentiate you as a results-oriented candidate.

This year, one of the hottest topics in CS was CSMs owning revenue. If you’re not tracking key metrics like NRR, GRR, and renewal rates, now’s the time to start.

Let me share an example from my own experience:

At the end of 2023, I closed my year with:

✔️ 112% Net Revenue Retention (NRR)
✔️ 95% Gross Revenue Retention (GRR)
✔️ 100% Renewal Rate

How did I get these numbers? I calculated these myself every quarter using ARR data from my leadership team.

Here’s the kicker: this information doesn’t always come directly from your manager. But when you can calculate these numbers and confidently share them, you’ll WOW your leadership.

If you’re unsure where to start, don’t worry—I’ve got your back.

Two years ago, I recorded a YouTube video that breaks down exactly how to calculate these metrics step-by-step. It went viral because it’s simple, actionable, and effective.

💡 What’s included in the video?

• A detailed walkthrough of calculating NRR, GRR, and Renewal Rates.

• A downloadable spreadsheet with the exact formulas I use.

• Insights into why tracking these metrics is a game-changer for your career.

👉 Check it out below:

Download the Excel spreadsheet here.

Owning your revenue and CS metrics isn’t just about numbers—it’s about demonstrating your value to your business. Let’s make 2025 the year you take full ownership of your success.

🎉 Wishing you a strong finish to 2024 and metrics that shine in the year ahead! 🎉 

Best,
Erika

P.S. If you enjoyed reading this newsletter, please consider sharing this edition with a friend.

Erika Villarreal

Hi {{ first name | there }},

It’s been a while—nine months, to be exact—since you last heard from me. First off, I want to say thank you for sticking around. I’ve missed this space and the connection we’ve built here.

I’ve had this email half-ready for weeks, trying to process everything that happened this year… my highs and my lows, and it is time to share it with you.

My Wins

✨ I was promoted to Strategic CSM at the beginning of this year. This role has stretched me in ways I didn’t expect, including managing my largest ARR customer yet—a global account that’s taught me more in a year than I could have ever imagined.

✨ I became a CS Insider Pathway program coach, guiding others in their CS career journeys.

✨ Alongside De’Edra Williams, I co-hosted Women of CS events in Dallas, connecting with inspiring CS professionals.

✨ I committed to a 5 a.m. workout routine Monday through Friday. I was very consistent and lost 10 pounds. I feel very strong and healthy!

✨ I sold my house in Mexico, which was a bittersweet but liberating milestone.

Setbacks

At the beginning of this year, I had ambitious goals for myself:

✨ Write bi-weekly for this newsletter.
✨ Reach 30K followers on LinkedIn.
✨ Write my third guide for CSMs

I was fired up and ready to make it happen, but life had other plans.

I lost momentum, and before I knew it, the weeks turned into months. Every time I sat down to write, no words came out.

The truth is, I needed to step back to focus on areas of my life that required my full attention. While my content creation took a backseat, I grew in other ways—and learned that it’s okay to reprioritize when life demands it.

Looking Ahead: Goals for 2025

As we approach a new year, I’m ready to set clear, actionable goals that align with my priorities:

🎯 Consistency: Publish at least 1 newsletter per month with valuable content for you.
🎯 Impact: Finally complete and launch my third guide for Customer Success professionals.
🎯 Networking: Reach 20K followers on LinkedIn by focusing on meaningful, value-driven content.
🎯 Health: Continue my fitness journey with a focus on strength and mindfulness.
🎯 Mentorship: Expand my role as a coach and give back to the next generation of CSMs.

This year has taught me that progress isn’t always linear, and sometimes, slowing down is the best way to speed up. I’m energized and excited to show up more consistently for you in 2025—starting now.

Here’s to learning, growing, and achieving together. 🚀 

Thank you for continuing to be here!

Best,
Erika