In Partnership With

Hey {{first_name | CS Pro}},

Everyone keeps telling you to be AI first, but nobody actually explains what that looks like on a Tuesday afternoon. So I sat down with Cassie Vaughn, who just left her role leading customer success across the Americas at Monday.com to become head of growth strategy at Clay, one of the most AI native companies out there.

She has built AI fluency into CS teams from both sides, and what she shared changed how I think about getting a team to actually adopt this stuff. Here is the thing, AI fluency is not about whether your team has opened ChatGPT. It is about whether they use it in a way that drives real results. Here is everything she shared including frameworks to help level up your entire CS team:

But first, today’s sponsor

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The trusted advisor trap

We throw the phrase trusted advisor around constantly in CS, and Cassie thinks we have it wrong. As she put it, the problem is that "people think that a trusted advisor is someone who has all of the answers and guides their customer or their advisee on how to get to those answers." Right now, nobody has all the answers, and AI is the most unknown area of everyone's world, so she uses the term thought partner instead. Your customers are excited about AI, a little nervous about it, and most of them feel like they should be further along than they are. What they actually want is someone to figure it out with them.

You do not need to have it all figured out. You just need to be in it with them.

The three layers of AI fluency

At Monday, Cassie built an AI fluency program with three parts.

1. The first is self-education, knowing the good podcasts, the voices worth following, and the basic language, like the actual difference between an LLM and an agent.

2. The second is communication, taking what you are learning and forming a real opinion so you can contribute and find your own voice.

3. The third is building, getting your hands on the tools, and as she points out, that is the part everyone rushes toward.

She is also clear that building well is not just typing a question into ChatGPT and hoping.

One line from a colleague at Clay stuck with her, and now it has stuck with me too: "Artificial intelligence is artificial and we have to remember that. It's not just intelligence. You have to give it native human intelligence for it to work appropriately." The reframe she would make now that she is starting over at Clay is that these three parts are not sequential steps you climb. They happen all at once, more like an open menu where you choose where to start.

Build a family of agents, and stretch your creativity

Here is the mistake Cassie sees everywhere. People think they need to build one all powerful agent that does everything a human does. Her advice is the opposite.

At Monday, her colleague Kim built a set of agents, a discovery agent, a build agent, and an optimization agent, that together act like a digital CSM. At Clay, Cassie is tinkering with an interview agent that nudges her during calls and drafts the scorecard after, while keeping a human firmly in the loop for the actual decision. AI is your co-pilot, and you are still driving. And the thing holding most of us back is not the tool, it is us.

As Cassie said, "the limiting factor most of the time in AI is our human ability to be creative." 

This week's challenge

Steal Cassie's exact starting move. Here is how she describes it:

Pick three AI podcasts and listen to two episodes a day, one on your way in and one on your way home. You are not trying to become the resident expert overnight, you are just getting close enough to the conversation to feel confident joining it. In her words, it "helped me feel, let's say 40% more confident in my ability to talk about it," and it is honestly the lowest effort place to begin.

Here are 3 AI podcast episodes from me that you can add to your playlist to help level up your AI skills:

• AI Is Not Replacing Customer Success… But It Is Exposing Bad CS

• Designing a Value Led Customer Success Organization with Jim Richmond

• How to Build Digital Success Plans That Actually Drive Adoption with Alana Stoltzfus

That is it for this week. If you want the full conversation, including how she is reimagining the entire customer journey at Clay, go have a listen on Spotify, Apple Podcasts, or YouTube. And as always, let me know what you think.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Join us LIVE in NYC for a community meetup →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest Munich →

Hey {{first_name | CS Pro}},

I have news that I have been waiting to share, and I am so excited it is finally happening!!!

On June 25, 2026, we are recording The Customer Success Pro Podcast LIVE for the very first time, in New York City.

This is not a webinar. This is the real thing, in a room, with real people, real conversations, and the kind of energy you only get when the CS community is together in person. We are bringing the show to life with a panel of leaders who are redefining what Customer Success can be, and you get to be in the room while it happens.​

The panel

• ​Anika Zubair, Host, The Customer Success Pro Podcast

• ​Cassie Vaughn, Global Head of Growth Strategy, Clay

• ​Chad Horenfeldt, Head of Customer Success, Avoca

• ​Malin Skoglund, VP of Growth & Strategic Deployment, Planhat

The evening agenda:

​5:30pm: Arrivals and drinks
6:00pm: Welcome from The Customer Success Pro
6:20pm: Live panel recording and audience Q&A
7:00pm to 8:00pm: Networking, drinks, and nibbles

​What you'll walk away with

• ​A clear view of where AI actually earns its keep in CS today, versus where it's still hype

• ​How leading teams are structuring their CS tech stack around AI, and the order they added tools in

• ​Practical plays you can take back to your team this quarter, not a year from now

• ​The honest version, including what these leaders got wrong before they got it right

🎟️ RSVP here: https://luma.com/m9ndhb0i

And NYC is only the beginning.

In 2026 we are working hard to bring the CS community together around the world, in different cities, throughout the year. More events are coming in the months ahead, and I want you to be the first to know when and where.

If you want to be notified the moment a new city is announced, sign up on our events page: https://www.thecustomersuccesspro.com/events

For now, all eyes are on New York.

Feel free to forward this email to your NYC bestie, and we hope to see you there. There are only 20 seats left for this live event, so RSVP soon!

See you in NYC,

Anika

Ps. There are only 20 seats left, RSVP now. Hope to see you soon!

Hey {{first_name | CS Pro}},

Last week we tackled the mindset behind commercial conversations. This week, it's time to get tactical. Because knowing you should be more commercial is one thing, and actually doing it on a live call with a customer you care about is a totally different beast. So here's my full playbook for talking about money without sounding slimy or salesy. Let's build the bridge.

The value bridge: five steps to a natural money conversation

Here's why this one works. It doesn't start with money. It starts with value, and it builds a logical path so that by the time you reach the commercial part, it feels obvious instead of awkward.

1️⃣ anchor in results. Start with what this exact customer has already achieved. Not a metric like "adoption is at 85%," but a business result like "your team cut onboarding from 45 days to 22 days." Business results are the currency of a commercial conversation.

2️⃣ name the gap. Point out where there's still untapped potential. You know which features they're underusing and which teams could benefit. Something like, "your customer-facing team uses the platform really well, but your ops team is still reporting manually. If we brought them in, that workflow could be cut in half."

3️⃣ quantify the impact. Put a number on it. "That's roughly 200 hours a year back, about $13,000 in recovered capacity, with a payback period under three months." You're not selling, you're doing the math your customer's CFO wants to see.

4️⃣ make the recommendation. This is where most of us bail and go passive with "just thought I'd flag it." Don't. Say, "my recommendation would be to expand your licenses to include the ops team. I can put together a proposal with scope, investment and timeline. Would that be helpful for our next meeting?"

5️⃣ navigate the response. They'll say yes, not right now, or push back on price. Stay curious and grounded in value. And if it's the price, do not defend it. Reconnect to the results instead.

3 scenarios you'll actually face

Renewals: open with the road ahead, not an apology. "Your renewal is about 90 days out. Before we get into logistics, let's step back and look at what we've accomplished and where we can drive even more impact." Then walk the bridge. By the time the paperwork lands, the renewal is a formality, not a negotiation.

Expansion: when a customer mentions a new team or initiative, transition with a story, not a pitch. "That's exactly the kind of use case where I've seen other customers get a big lift from this feature. Can I share a quick example?" It's pattern recognition, not pressure.

The dreaded "we're evaluating other options": breathe. This is information, not rejection. Ask, "what's driving the evaluation? Is there something specific you're not getting from us, or is this a standard procurement process?" That one question tells you whether it's a real threat or a checkbox exercise.

5 tips that will help

1. Pre-frame it. At kickoff, tell customers that commercial conversations are standard practice, not a warning. They'll see you as more strategic for it.

2. Use "my recommendation," not "I think you should." One sounds like an opinion, the other sounds like professional counsel.

3. Speak their language. If their VP said "operational efficiency," use those exact words back, not your internal jargon. It feels like listening, not selling.

4. Practice the pause. After you share a number or a recommendation, stop talking. Don't rush to fill the silence with "but no pressure." Silence communicates confidence.

5. Document in business impact. Follow up with a summary tied to outcomes, not features. That email does more for your credibility than the call ever could.

Your Weekly Challenge

Last week I asked you to identify one customer where you see a commercial opportunity and write down what you'd say. This week, go have the conversation. Pick one call, a review, a check-in, whatever you've got, and run the value bridge. Anchor in their results, name a gap, quantify it even if it's rough, make a real recommendation, then navigate their response.

Afterward, write down three things: what went well, what felt uncomfortable, and what you'd do differently next time. That reflection is where the growth happens, because this is a skill, and skills get sharper with reps.

Then take a screenshot and tag me on LinkedIn. I want to be your accountability coach and celebrate the win with you.

Want all the language and scripts in full? Have a listen to the latest episode on Spotify, Apple Podcasts, or YouTube, and let me know what you think.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Apply to join RevUP Academy in 2026 →

Download tons of CS resources from my library →

Come join us at TCSP LIVE in NYC →

In Partnership With

Hey {{first_name | CS Pro}},

Ever had that moment where you see an expansion opportunity sitting right in front of you…and you just don't bring it up? Yeah, me too. Nearly half of all CSMs feel the exact same way. This week on the podcast, I am kicking off a two part series about moving from friendly to commercial. Part one is all about what is going on in your head, because if we do not fix the mindset first, no script is going to save you.

But first, today’s sponsor

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Retention comes down to trust. Check-ins and good intentions help, but consistently showing customers the value they’re getting, in their own data, is what drives renewals.

This ebook walks through the step-by-step process for using data-driven content across the customer lifecycle to earn and sustain customer trust. 

Inside, you will find:

• Why trust is the foundation of retention (especially in a downturn)

• How to map data-driven content to each stage of the customer journey

• The key components every piece of customer-facing content needs

• How Asana, Autodesk, Greenhouse, and Okta put this into practice

The Real Reason You Avoid Talking About Money

According to ChurnZero's CSM Confidential Report:

Not product knowledge. Not time management. The commercial side of the job.

And honestly, it makes sense. Psychology Today found that money conversations are one of the most universally avoided topics in human interaction. Combine that discomfort with a profession built on empathy and being the customer advocate and you get CS pros who are incredible at building trust but freeze the second it is time to talk commercially. That is not a personal failing. It is a systematic gap in how our industry was built.

The core problem is not that CSMs cannot sell. It is that most do not see themselves as someone who should sell. You spend months building an incredible relationship, then when the expansion moment shows up, you either pass it to sales, avoid it, or water it down to something like, "just a heads up, the renewal is coming up." That is not a commercial conversation. That is a throwaway comment.

The 5 Mistakes Keeping You in the Friend Zone

I have made every one of these myself, so no judgment. But naming them is how we fix them.

1️⃣ treating the word "commercial" like a dirty word. Being commercial just means you understand the business value of what you deliver and can articulate it. When a doctor tells you that you need surgery, you do not think they are being salesy. You think they are being direct and helpful.

2️⃣ waiting for permission to talk about money. If you are waiting for the customer to bring up the renewal or for sales to loop you in… you will always be too late.

3️⃣ leading with product instead of outcomes. Saying "we just launched this new module" is a product pitch. Tie it back to the business problem your customer is trying to solve instead.

4️⃣ apologizing before you start. "Sorry, I have to put my sales hat on for a second"… cringe. Research shows buyers are three times more likely to disengage from someone who avoids pricing discussions. The apology makes things worse.

5️⃣ separating value from revenue in your mind. When customers get value, they renew. When they get more, they expand. Revenue is not the opposite of value. Revenue is proof of value.

What to Do Instead

Redefine what commercial means to you. Stop associating it with pushy and start associating it with responsible. If you have all this knowledge about a customer's business and do not bring up opportunities that could help them… that is not being friendly. That is being negligent.

Detach your identity from the outcome. If a customer says no to an upsell, that is not a rejection of you. That is information. You are doing what a strategic advisor does, giving a recommendation.

Build commercial habits into everything you do. Every business review should include future growth opportunities. Every success plan should have a commercial milestone. When it is part of your rhythm, it stops feeling scary and starts feeling normal.

And learn the language of business. Your CFO does not care about health scores. They care about ROI, cost savings, and growth. When you connect product value to those conversations, talking about money is expected.

Your Weekly Challenge

Pick one customer this week. Just one. Write down the answers to these three questions.

1. What business outcome is this customer trying to achieve? Not features, the actual business goal.

2. Is there an opportunity for them to get more value from something they have not explored yet?

3. If you were going to bring this up in your next conversation, what would you say? Not a pitch. Just how would you naturally introduce it?

Write it down. Do not overthink it. You are building the muscle of connecting value to commercial opportunity.

Have a listen to the full episode on Spotify, Apple Podcasts, or YouTube and let me know what you think!

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Apply to join RevUP Academy in 2026 →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest Paris & Munich →

In Partnership With

Hey {{first_name | CS Pro}},

A lot of teams think they are multi threaded because they have a few names on the account. But having a few contacts is not the same as having real influence. This week’s podcast episode with Brittany Casey is a powerful reminder that if your relationships do not go deep enough, your revenue is more fragile than you think.

But first, today’s sponsor

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Your CS team is still figuring out AI. Here’s how other teams are actually doing it.

Everyone's talking about what AI could do for CS teams. The AI + Post Sales Summit is where you'll see what teams are actually doing: real workflows, real demos, real results.

Hosted by Matik on Thursday, June 4, this free event is built for post-sales teams who want to go beyond the theory.

Here’s what’s included:

• Virtual sessions - show & tells from practitioners using AI across the post-sales journey

• Competition - submit your AI workflow, get judged by industry experts, and win prizes

In-person workshop - collaborate, troubleshoot, and build connections with peers

Multi Threading Is More Than More Names

One of my favorite parts of this conversation was how clearly Brittany broke down the difference between having contacts and having coverage.

Because let’s be honest, a lot of CSMs can pull up an account and point to three or four people they know. But when renewal season hits, they are still relying on one champion to do all the internal selling. And that is where things start to fall apart.

Multi threading is not just about quantity. It is about relevance, influence, and consistency.

Brittany made the point that you cannot really understand an account unless you are hearing from different levels of the business. That means understanding the goals of the day to day user, the admin, the department lead, and the executive sponsor. And those goals are not always the same.

The end user may care about speed and ease. The admin may care about process and adoption. The executive may care about cost, efficiency, risk, or growth. If you are only speaking one language to all of them, you are missing the mark.

And this is exactly why multi threading matters so much right now. Buying decisions are more complex, more stakeholders are involved, and every investment is being scrutinized more closely. If you do not have relationships across the account, you are not just missing expansion opportunities. You are putting renewals at risk.

The Best CSMs Are Quiet Quarterbacks

Brittany said something in this episode that really stuck with me. She described the CSM as the quiet quarterback on the account.

That is such a good way to think about this role.

You are not supposed to do everything yourself. You are supposed to understand the full field, know what play needs to happen next, and bring in the right people at the right time. Sometimes that is sales. Sometimes that is enablement. Sometimes that is your executive team. Sometimes that is your customer champion.

This matters because one of the biggest mistakes CSMs make with multi threading is treating it like a solo job.

Your sales counterpart likely knows who signed the contract, who pushed the deal through, what objections came up, and where the real power sits. Your leadership team may already have connections with senior stakeholders inside the account. Your internal teams might have relationship context you do not even know exists yet.

So instead of putting all the pressure on yourself, think like a strategist.

Use relationship mapping as a team sport. Build it with sales. Revisit it with leadership. Pull in internal context. Look for gaps. Ask yourself where you have influence, where you do not, and who can help you close that gap.

And most importantly, do not treat the relationship map like a one time exercise.

Brittany was clear on this. The map should be a living document. It should evolve as people move roles, priorities change, and risk shifts inside the account. Because customers are not static, and your account strategy cannot be static either.

Real Partnership Is What Drives Revenue

Another point I loved from Brittany was this idea that customers are not just buying software. They are buying partnership.

That is such an important reminder in a world obsessed with features, AI, and product launches.

Customers stay when they believe you understand their business, can help them navigate change, and can bring value through complexity. They renew when they trust the partnership, not just the platform.

And that is where strong multi threading becomes such a growth lever.

When you build relationships across departments, levels, and priorities, you stop relying on one person to carry the account. You create resilience. You create more visibility. You create more opportunities to uncover value and tell that value story in a way each stakeholder actually cares about.

Brittany also shared a really smart tactic here. When you hit a wall trying to build deeper relationships, look for people inside the customer account who can help you influence from within. Maybe it is your champion. Maybe it is someone who wants more visibility. Maybe it is someone who is ready to become an internal advocate.

If you can help that person succeed, you are not just supporting adoption. You are helping create internal momentum for your partnership.

That is where multi threading gets powerful. It stops being a box checking exercise and starts becoming a real revenue strategy.

Maybe that is looping in sales to map stakeholders together. Maybe it is setting up a value conversation with a different department lead. Maybe it is asking your champion to introduce you to someone more senior.

Just start.

Because the truth is, accounts do not become multi threaded by accident. They become multi threaded because someone leads with intention.

That’s it for this week. If this episode made you rethink how strong your customer relationships really are, go listen to the full conversation with Brittany Casey. It is packed with practical advice for any CSM or CS leader who wants to protect revenue, build deeper partnerships, and stop being one resignation away from risk.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Apply to join RevUP Academy in 2026 →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest Paris & Munich →

In Partnership With

Hey {{first_name | CS Pro}},

Let me be clearn, AI is not taking your job. Well not your whole job. But it is making one thing very clear…whether you were ever truly adding value in the first place.

And if that feels uncomfortable, good. Because this is the shift that will define your career.

Today I want to make sure that your job stays ‘AI-proof’ which is why I wanted to dive into all the BAD customer success that will be replaced by AI.

But first, today’s sponsor

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How Leading CS Teams Are Running Their Business Reviews

Most business reviews follow the same pattern: pull data, build slides, present, repeat. But the teams driving real retention results do something different with that data.

Matik's Show & Tell series brings together top CS teams to share exactly how they run business reviews and customer presentations, with strategy, structure, and real examples included.

Learn from:

• Glassdoor's approach to highlighting ROI

• Salesloft's strategy for guiding reps to drive impact

• 6sense’s method to ensure retention and growth

AI is not the threat… your old role is

Let’s just call it what it is.

For years, a lot of customer success work has been built around activity. Sending follow ups. Running check ins. Tracking usage. Updating CRM. Building reports.

And now?

AI can do all of that in seconds.

That is where the panic is coming from. Not because AI is replacing Customer Success, but because it is stripping away the parts of the job that were never strategic to begin with.

If your value was based on how fast you could send an email or how many calls you ran in a week… that value is gone.

I just want to be really clear, that is a GOOD thing.

Because it forces you to step into the version of the role that actually matters.

The biggest mistake teams are making with AI

Here is what I am seeing everywhere right now. CS teams are using AI to do MORE… instead of doing BETTER.

• More emails.

• More summaries.

• More content.

• More touchpoints.

But let me ask you something…If you were the customer, would you want that?

No.

Your customers are already overwhelmed. AI has made content easier to create, which means there is now more noise than ever. And adding to that noise does not make you valuable.

It makes you ignorable.

AI should not increase your volume. It should increase your IMPACT.

The second mistake I am seeing… over automation.

Automated check ins. Automated journeys. Automated engagement.

And while that sounds scalable, what it actually creates is distance.

Customers do not feel understood. They feel processed.

The final mistake…outsourcing your brain.

Yes, AI is powerful. Yes, you should be using it.

But if you are blindly trusting it, copying outputs, or letting it do your thinking… you are losing the one thing that actually makes you valuable:

• Your judgment.

• Your experience.

• Your ability to read the room.

AI can support that. It cannot replace it.

What the best CS Pros are doing differently

So if AI is taking all the admin work off your plate… what is actually left?

The best CSMs right now are doubling down on three things.

1. Outcome design.

They are not talking about features or usage. They are defining what success actually looks like for the customer… in business terms.

Revenue. Efficiency. Risk reduction.

And they are building a plan to get there.

2. Executive communication.

They are not running status updates.

They are leading conversations.

They know how to speak to decision makers. They understand what matters at the top level and they connect everything back to business impact.

Because here is the truth… executives do not care about your dashboard. They care about results.

3. Revenue thinking.

They understand where the risk is in an account. Where the opportunity is. What the expansion path looks like.

AI can give you data.

But it cannot decide what to DO with that data.

That is your job.

And this is the line I want you to sit with…

If AI can do your job, your job was never strategic to begin with.

Weekly Challenge

Take one task you currently do manually.

Ask yourself… can AI do this faster?

If the answer is yes, automate it.

Immediately.

Then take that time back and reinvest it into ONE strategic conversation with a customer.

Not a check in.

Not a status update.

A real conversation.

Ask about their business goals. Their biggest challenges. Where they are trying to go.

And then connect your product to that.

That is where your value lives.

That is how you stay ahead.

The reality is, AI is not lowering the bar in customer success… it is raising it.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Check out the latest CS Insider Report featuring TCSP →

Download tons of CS resources from my library →

TopCSJobs featured TCSP podcast as a top podcast to listen to→

Hey {{first_name | CS Pro}},

Customer Success didn’t slowly evolve…it shifted overnight (thanks AI 🙄 ). And now you’re being asked to own revenue without ever being taught how.

If you’ve felt that pressure lately, you’re not behind…you’re just operating in a role that changed faster than your training.

13 years ago when I was a CSM I was taught differently. Onboarding, support, customer happiness was what I was trained for. And to be fair that is what CS did for a long time and it was working, until it wasn’t. This new era of CS has hit us all very quickly and it is all about adapting or being left behind. Let’s talk about the new modern Customer Success that is infront of us now…

But first, today’s sponsor

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Renewals should not feel stressful, last-minute, or reactive.

Yet for most CSMs, they still do.

Not because they lack effort, but because customers are not clearly connecting your work to THEIR business outcomes.

That is exactly what this free live masterclass is designed to fix.

Join me for a BRAND NEW live masterclass session where I will walk you through the framework I use to help CSMs move from check in calls to outcome led conversations that customers actually value.

Join live and learn how to start driving revenue, not just managing accounts.

⏰ Wednesday, April 29th at 10 am PT / 1pm ET / 6pm UK

🔗 Save your spot now: thecustomersuccesspro.com/masterclass

Customer Success Got a Promotion (Without Training)

Let’s call it what it is. The world economy is in a state of flux. No one is saying it is a recession, but there is very little stability which means…

Customer Success has officially become a revenue function.

You’re now expected to forecast renewals, drive expansion, and influence pipeline. But the reality is…most teams were never trained to do any of that.

So what happens?

You end up in this weird in between space.

You’re running check ins, answering emails, supporting customers, but at the same time, leadership is asking you about forecast accuracy, expansion pipeline, and NRR targets.

And those two worlds do not match.

This is why so many CSMs feel stuck right now. Not because they’re not capable, but because they’re being measured like sales, while still operating like support or account management.

And let’s be clear about something. This shift isn’t random.

Budgets are tighter. Growth is harder. Investors care more about expansion than ever before.

Which means the fastest way to grow a business is no longer new logos…it’s existing customers.

And that puts YOU at the center of revenue.

The Mistakes That Are Quietly Killing Your Revenue

Now here’s where it gets uncomfortable. Because most of the things that used to work in Customer Success… don’t work anymore.

The biggest one?

Believing that strong relationships lead to revenue. (I know. This one stings.)

You can have amazing rapport, great calls, happy customers…and still lose the renewal.

Why?

It comes from delivering and proving outcomes.

Another mistake I see all the time is staying in “helpful mode.”

Answering questions. Walking through features. Solving tickets.

That work feels valuable… but it’s not what drives revenue.

And here’s the reality…AI is already taking over a lot of that.

So if your value is based on being helpful, you’re going to stay busy… but not impactful.

And then there’s the biggest one.

Treating renewals and expansions like events.

Waiting until 60 or 90 days before renewal to talk about value.

At that point, it’s already too late.

Revenue is not built at renewal.

It’s built in every single interaction leading up to it.

3 Skills That Change Everything

If you want to actually succeed in this new version of Customer Success, there are three skills you need to master.

And no, they are not product knowledge or relationship building.

1. Commercial Discovery

You need to understand how your customer’s business actually works.

How do they make money?

Where are they losing money?

What are their top priorities this quarter?

If you don’t know this, you cannot drive revenue.

Because your product is not valuable on its own… it’s only valuable in the context of their business.

2. Value Articulation

This is where most CSMs fall short.

You need to clearly connect your product to business outcomes.

Not features. Not usage.

Impact.

You should be able to say:

If you can’t say that with confidence, renewal conversations will always feel hard.

And expansion will feel impossible.

3. Expansion Strategy

Expansion is not about selling more.

It’s about solving more problems.

Where are the gaps in adoption?

Where are new use cases?

Where is there unrealized value?

When you approach growth this way, it stops feeling like selling… and starts feeling like helping at a strategic level.

And that’s when customers say yes.

Weekly Challenge

This week’s challenge one is simple…but powerful.

Pick ONE account. (Just one!!!!)

And answer these three questions:

1. What is this customer’s top business priority right now?

2. How is your product directly impacting that priority?

3. Where is there an opportunity to expand value?

If you cannot answer any of these clearly…that is your gap.

And that gap is exactly where revenue is being lost.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news, events, podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

AI alone won't save your account. This will →

Zoom CX Summit: From Insight to Impact →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest →

Hey {{first_name | CS Pro}},

Most teams do not have a churn problem. They have a timing problem. They are waiting until renewal risk is loud, obvious, and painful, when the truth is the customer started drifting way earlier.

In this week’s podcast episode, I sat down with Julie Fox, Director of Digital and Scaled Customer Success at Hyland, to talk about how modern CS teams can stop reacting so late and start using customer data to forecast revenue more proactively.

(youtube) https://youtu.be/BAeZgZQuYEM

But first, today’s sponsor

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Renewals should not feel stressful, last-minute, or reactive.

Yet for most CSMs, they still do.

Not because they lack effort, but because customers are not clearly connecting your work to THEIR business outcomes.

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Join me for a BRAND NEW live masterclass session where I will walk you through the framework I use to help CSMs move from check in calls to outcome led conversations that customers actually value.

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⏰ Wednesday, April 29th at 10 am PT / 1pm ET / 6pm UK

🔗 Save your spot now: thecustomersuccesspro.com/masterclass

Symptoms, not signals

That line from Julie really stuck with me.

Because when a customer stops replying, starts sounding vague, or suddenly shows up red in your health score, most teams treat that as the moment to act. But by then, the damage has usually already been done.

The customer has already felt friction. They have already questioned the value. They have already started deciding whether your product is worth renewing.

And that is exactly why this conversation matters so much.

Julie shared that in scaled and digital customer success, the goal is not just to track activity. It is to understand behavior patterns over time. Not just who logged in, but how they are using the product. Not just whether they submitted support tickets, but what those tickets are telling you. Not just whether they attended a webinar, but whether their behavior moved closer to meaningful adoption after that.

That is the difference between reactive churn management and proactive revenue forecasting.

Too many teams are still spending all their energy swarming red accounts right before renewal. They roll out the red carpet, throw in extra meetings, and hope that more attention will somehow save the account.

But that is exhausting for your team, overwhelming for your customer, and honestly, not very effective.

Julie’s approach is much smarter.

Instead of obsessing over who is already on fire, she looks at earlier indicators like declining usage depth, feature abandonment, lack of adoption across multiple users, weak expansion into core workflows, and long gaps between meaningful actions.

That is where the real story lives.

Because churn is rarely caused by one big dramatic moment. It is usually a series of small missed moments that pile up over time.

The best scaled CS teams think in journeys, not just accounts

One of the things I loved most about Julie’s perspective is that she does not define digital customer success as just sending emails at scale.

She defines it as designing the full customer experience.

That means looking beyond just CS touchpoints and thinking about the entire journey. Product. Support. Marketing. Education. Community. In app guidance. Human support when it is needed.

And honestly, that is the mindset more teams need.

If you are managing thousands of customers, you cannot just copy and paste your enterprise model and hope it works. You also cannot solve scale by throwing more bodies at the problem

You need to understand what customers actually need, when they need it, and how they want to receive support.

Some customers want human interaction. Others do not want a meeting unless it is absolutely necessary. Some want answers directly inside the product. Others want a webinar, a guide, or a quick piece of educational content they can use on their own time.

That means scaled CS is not about removing the human touch. It is about being far more intentional about when and where human effort adds the most value.

Julie talked about starting with customer journey mapping, and I could not agree more.

If you want to get smarter about churn and forecasting, you need to map two things.

First, what you expect customers to do throughout their journey.

Second, what success actually looks like from their point of view.

Those are not always the same thing.

And when you can line those two things up, you start spotting the gaps earlier. You can see when a customer is technically active but not actually progressing. You can see when someone bought a product but has not integrated it into their workflow. You can see when there is usage, but no depth. Motion, but no value.

That is the kind of insight that gives you leverage.

Revenue forecasting gets better when your signals get smarter

Julie made a point that I think every CS leader needs to hear. One of the hidden benefits of digital CS is better forecasting.

Not because the data is magically perfect. It is not.

But because when you build consistent ways of identifying risk early, understanding customer behavior, and running targeted interventions, your forecasting becomes far more credible.

Instead of saying, “These accounts are up for renewal and some of them feel risky,” you can say, “Here is what is happening, here is why it matters, and here is what we are doing about it.”

That is a very different conversation.

Julie broke this down into three layers she looks at when analyzing churn risk.

Quantitative patterns, things like product usage, support activity, and engagement data.

Customer context, things like lifecycle stage, stakeholder changes, use case maturity, and industry complexity.

Outcome alignment, which is the big one. Are customers actually achieving what they bought the product for?

That last one matters most.

Because a customer can be busy, engaged, and still not be getting meaningful business value.

And if you cannot clearly tie their current experience back to revenue, cost savings, or risk reduction, then your renewal story is weak no matter how many check in calls your team had.

I also appreciated how honest Julie was about forecasting. She said what a lot of people are afraid to admit, when you first start, some of it IS guesswork.

And that is okay.

The goal is not perfection on day one. The goal is to get better over time.

Try a model. Learn from the outcomes. See where your health scores were wrong. Look at which green accounts actually churned. Adjust. Improve. Keep layering better signals into your process.

That is how you move from reactive forecasting to predictive forecasting.

Not by pretending your data is perfect, but by getting more disciplined about how you use the data you do have.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Apply to join RevUP Academy in 2026 →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest →

Hey {{first_name | CS Pro}},

The FREE CS Pro Masterclasses are back for 2026, and we are kicking off with the topic YOU asked for.

I polled the CS Pro community, and you all wanted one clear topic covered in our next masterclass, which was….

“How to show value to customers for renewals”

And the time has come….

If the end of 2025 was a rush to hit last-minute renewal pressure, awkward value conversations, and accounts that slipped because customers could not clearly see the impact, this is for you.

Renewals should not feel stressful, rushed, or reactive.

Yet for most CS Pros, they still do. Not because you are not working hard, but because customers are not connecting your work to THEIR business outcomes.

Not because you are not working hard, but because customers are not connecting your work to THEIR business outcomes.

That is exactly what this brand new 2026 masterclass is designed to fix.

THE CS REVENUE FRAMEWORK
The 3 Step Value System for Renewals and Revenue Conversations

In this free live session, I will walk you through the exact framework I use to help CS Pros move from check in calls to outcome led conversations that customers actually value.

In this masterclass, you will learn how to:

• Shift from activity driven check ins to outcome focused conversations

• Clearly show value in every customer interaction, even without a perfect product

• Build momentum toward renewals and expansion instead of scrambling at the last minute

This framework is the foundation for predictable renewals, stronger customer relationships, and hitting your KPIs with confidence as you start the new year.

If you are done hoping renewals work out and ready to take control of your numbers, this is the closest thing to a guarantee you can give yourself in 2026.

Come join us LIVE:
⏰ Wednesday, April 29th
10am PT | 1pm ET | 6pm UK

🔗 Save your spot now: thecustomersuccesspro.com/masterclass

Spots are limited, and this is a live session, so make sure you register early.

See you live,
Anika

P.S. — Over the next few weeks you will be hearing more from me about RevUP Academy. If the timing is not right for you, no hard feelings. Simply click here to snooze these emails for the next week. Just know that means you will miss reminders, updates, and early access when doors open.

Hey {{first_name | CS Pro}},

Renewals are rarely won or lost on the renewal call. They are decided months earlier through the value your customer actually experiences.

If renewals feel stressful or unpredictable, it usually means the real work is happening too late in the customer journey.

Let’s break down what is actually happening.

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Renewals Are Decided Long Before Pricing

Right now every SaaS board and executive team is obsessed with one metric. Net Revenue Retention.

And it makes sense. Capital is tighter, budgets are under scrutiny, and companies are realizing something that has always been true. It is much cheaper to retain and expand existing customers than it is to acquire new ones.

But here is the problem most teams are missing.

Retention does not happen during the renewal cycle. It happens during value realization.

Many CS teams still treat renewal like a late stage sales process. The playbook kicks in around 90 days before contract expiration. The CSM schedules a renewal prep call, pulls together a slide deck, shares product metrics, and reviews everything the team has done for the customer.

On paper, everything looks fine.

Usage is decent.

There are no open escalations.

The relationship with the champion feels good.

Then the customer says something like this.

“We are evaluating our budget and not sure we are getting enough value.”

Or worse.

“We are exploring other options.”

And suddenly the account feels at risk.

Here is the truth most teams overlook.

Renewals are emotional decisions wrapped in financial language.

If a customer has not experienced clear and measurable progress toward their goals, the renewal call simply becomes the moment they finally say it out loud.

The renewal conversation does not create churn.

It reveals churn that has already been building for months.

What Most Customer Success Teams Get Wrong

Over the years I have seen the same patterns appear again and again in Customer Success teams.

These small mistakes slowly erode value long before the renewal conversation ever happens.

The first is treating onboarding like implementation instead of transformation.

Many onboarding programs focus heavily on product setup. Integrations. Feature walkthroughs. Training sessions.

All of those things matter. But they are not the outcome your customer actually bought.

Your customer did not purchase software.

They purchased progress.

Ninety days before signing your contract they had a business problem they were trying to solve. A gap in their process. A revenue opportunity they wanted to unlock. A risk they wanted to reduce.

If onboarding focuses only on product setup and not on the transformation they were hoping to achieve, you are leaving your renewal to chance.

The second mistake is failing to document success in a meaningful way.

Many teams create success plans during onboarding. Then those plans quietly disappear into a folder somewhere.

Even worse, the plan often does not connect to a commercial outcome that matters to the customer.

If you cannot clearly articulate what the customer is trying to achieve, how you are measuring progress, and what success looks like in financial terms, then the renewal becomes subjective.

And subjective value is dangerous.

Because when budgets get tight, subjective value is the first thing that gets cut.

The third mistake is relying too heavily on a single champion.

Most accounts begin with several stakeholders involved. Sales introduces the executive buyer, the implementation team, technical contacts, and financial stakeholders.

But over time many CSMs default to working only with the day to day champion.

While that relationship may be strong, the renewal decision is rarely made by that person alone.

If you are not aligned with the budget owner or executive leadership, your renewal is sitting in the hands of someone without decision authority.

That is a risky place to be.

The final mistake is saving value conversations for Quarterly Business Reviews.

If the only time you discuss ROI is during a formal quarterly presentation, value will feel artificial and distant from everyday product usage.

Value needs to feel continuous.

Your customer should feel progress every time they interact with your product.

How to Build Renewals That Feel Predictable

Instead of reacting to renewal risk late in the cycle, the best Customer Success professionals design renewals from day one.

It starts with anchoring the entire relationship in a revenue success plan.

A strong success plan is not a checklist.

It is a living document that connects three things.

The customer’s strategic business goals.

The measurable outcomes tied to those goals.

And how your product contributes to achieving them.

Every major customer conversation should tie back to this plan.

What progress have we made since our last conversation?

What measurable impact can we point to?

What milestone are we working toward next?

This keeps the relationship grounded in outcomes rather than activity.

It also helps you track leading indicators of renewal risk much earlier.

Instead of focusing only on usage or NPS, look at signals like executive engagement, adoption depth across teams, and alignment with the customer’s current company priorities.

Two additional factors are especially important.

You should know when your customer’s budget decisions actually happen.

And you should know who has the authority to approve that budget.

Those two pieces of information can dramatically change how you approach renewal strategy.

The most successful CSMs also treat every conversation as a value conversation.

Even regular check ins should answer three simple questions.

What progress have we made?

What impact are we seeing?

What is the next milestone?

When you start these conversations 120 days or more before renewal, the renewal itself feels like a continuation of strategy rather than a negotiation about price.

Weekly Challenge

Pick one account that is renewing within the next six months.

Then ask yourself three questions.

1. Can you clearly articulate the customer’s top three business goals for this year?

2. Do you have quantified evidence showing progress toward those goals?

3. Have you validated that value with an executive level stakeholder in the last 90 days?

If the answer to any of these questions is no, that renewal may already be at risk.

Schedule a value alignment conversation with that customer this week.

Do not frame it as a renewal conversation.

Frame it as a strategy or value realization conversation instead.

Because the best Customer Success professionals do not scramble to save renewals.

They design them.

Quarter by quarter. Conversation by conversation. Outcome by outcome.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

💻️ Anika’s Desk:
_{Here are a few links, books, news podcasts or anything else that might feature Anika or come across her desk that might be helpful to you:}

Book a call to discuss a team workshop →

Apply to join RevUP Academy in 2026 →

Download tons of CS resources from my library →

Come hear me speak at SaaSiest →

Hey {{first_name | CS Pro}},

If a customer asks for a discount at renewal and your stomach instantly drops, you are not alone. But today’s newsletter is going to give you real reason why discounts come up.

A discount request is rarely about price. It is almost always about value.

This week on the podcast, I break down exactly how Customer Success Pros should handle renewal discount requests without panicking, without immediately conceding, and without damaging the relationship.

Because that moment when a customer asks for a discount? It is actually one of the biggest signals about how your entire year of customer conversations has gone.

And if you handle it the right way, it can completely shift how your customers see your value.

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Discount requests are rarely about price

Over the past few years, SaaS companies everywhere have tightened budgets. CFOs are reviewing every line item. Finance teams are asking departments to reduce spend across the board.

And guess what sits on that spreadsheet?

Your software. 👀 

So when a customer asks for a discount, it does not automatically mean they are unhappy with your product or your work as a CSM.

Often it simply means someone in finance said something like:

“Reduce software spend by 10% this year.”

The person you work with internally now has to justify every tool in their tech stack.

And that means your renewal becomes a conversation about value.

The mistake most CSMs make in this moment is assuming the conversation is about price.

So they panic.

They say things like:

“Let me check with my manager.”

“Let me see if we can approve that.”

“Maybe we can do 10%”

But the second you treat the conversation as a pricing issue, you have already lost the value conversation.

The real question you should be asking is this:

What is actually driving the discount request?

Because price is usually just the symptom. Not the problem.

The mistakes that lead to discount conversations

When discount requests appear at renewal, it usually points to something that happened much earlier in the relationship.

Here are a few patterns I see all the time.

1. Value was never clearly positioned during the year.

If your customer conversations were mostly feature updates, check ins, or product walkthroughs, then when renewal arrives the only lever left to discuss is price.

Customers negotiate price when ROI is unclear.

2. CSMs negotiate against themselves.

I see this happen constantly.

A customer asks for twenty percent.

The CSM responds with:

“Maybe we could do ten percent.”

Without any negotiation.

Without any discussion.

Without any value conversation.

That is not negotiation. That is fear based selling.

And the reality is you do not even know if the customer actually needs the discount. Many times they are simply testing whether you will give one.

3. Teams fail to diagnose the real issue.

A discount request might actually be caused by something completely different.

Low adoption.

A new executive sponsor.

A feature misunderstanding.

Procurement pressure.

If you do not diagnose the root cause, you cannot respond strategically.

And finally, many Customer Success teams detach from revenue ownership.

The moment pricing comes up, the conversation gets handed off to sales or account management.

But here is the reality.

A renewal is a sale.

If you own renewals, you are responsible for leading the value conversation.

That includes negotiation.

Respond strategically instead

So what should you actually do when a customer asks for a discount?

First, slow down.

You do not need to respond immediately. In fact, reacting instantly usually leads to bad decisions.

Instead say something like:

Stay calm. Stay curious. Diagnose the situation.

Second, shift the conversation to outcomes.

Ask questions that bring the conversation back to impact:

What goals are your top priorities this year?

How are you evaluating the impact of our platform internally?

What would make this renewal feel like a no brainer?

These questions move the conversation away from price and toward value.

Third, anchor the conversation in ROI.

Instead of defending the price, quantify the impact.

For example:

Over the past twelve months your team increased adoption by thirty seven percent, reduced onboarding time by two weeks, and drove over one million dollars in influenced revenue tied to the workflows we implemented.

When ROI becomes clear, price becomes easier to justify.

Fourth, trade instead of conceding.

If there truly is budget pressure, do not give discounts for free.

You can exchange value for value.

Examples might include:

• Multi year commitments

• Adjusted seat counts

• Reduced scope

• Phased rollouts

Discounting without a trade erodes the perceived value of your product.

And finally, bring the right stakeholders into the conversation.

Procurement is always focused on reducing cost.

But your executive sponsor understands the impact your product delivers.

When those voices are part of the same conversation, the value becomes much harder to ignore.

Weekly Challenge

Before your next renewal cycle, do this exercise.

Look at your top five upcoming renewal accounts and write down three things for each one.

One quantified outcome the customer achieved.

One executive level goal you are aligned to.

One risk if the customer did not renew.

If you cannot clearly answer these three questions, your renewal is vulnerable to a discount conversation.

But if you can answer them, you will walk into that renewal with confidence.

Because when value is crystal clear, price becomes much harder to challenge.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

Book a call to discuss a workshop

Hey {{first_name | CS Pro}},

What does it actually take to build a value-led customer organization?

In this week’s podcast, I sat down with Jim Richmond, Chief Customer Officer at Smartling, to talk about how CS teams need to evolve… especially in a world where AI is moving faster than most teams can keep up.

And one thing became very clear during our conversation.

Most CS teams are still structured around tasks, not outcomes.

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Why Most Customer Organizations Are Still Task-Driven

Many customer success teams say they are “value driven”, but when you look closely at how they actually operate, the work still revolves around tasks.

Running meetings.

Answering tickets.

Sending follow ups.

Tracking product usage metrics.

Sound familiar?

Jim shared that when he first looked at Smartling’s customer conversations, the focus was largely on internal metrics. Things like translation volume, feature usage, or cost per word.

But customers didn’t actually care about those metrics.

What they cared about were business outcomes.

Entering a new market.

Reducing regulatory risk.

Launching products faster in new regions.

So the team made a major shift. Instead of talking about product usage, they reframed conversations around what customers were able to accomplish because of the product.

In other words…they moved from software metrics to business outcomes.

And that single shift completely changed the dynamic of their customer conversations.

The Problem With Traditional QBRs

Jim shared something that I absolutely loved.

He decided to completely redesign their QBR structure.

Not eliminate them… but rethink what they were actually for.

Because let’s be honest. Traditional QBRs often feel repetitive and product focused. Slide after slide about features, usage metrics, and roadmap updates.

That’s not valuable for most customers.

So instead, his team introduced themed business reviews throughout the year.

The first review focuses on defining what success actually looks like for the customer. What metrics matter to them? What business outcomes are they trying to achieve?

The second review focuses on proactive recommendations. What should the customer do next to hit those goals?

The third review becomes a mid year progress check.

And the final review focuses on planning the next year together.

The key difference is this: every review centers around the customer’s metrics… not the product’s metrics.

That shift forces the CSM to think differently.

Instead of asking “How are they using our software?” the better question becomes:

“What are they trying to accomplish in their business?”

Why Specialized Roles Are The Future of CS

Another major insight from our conversation was how Smartling redesigned their customer organization.

For years, many CS teams relied on the generalist CSM model.

One person handled everything.

• Onboarding.

• Adoption.

• Reporting.

• Renewals.

• Expansion.

But as companies grow and products become more complex, that model starts to break.

Jim’s approach was to specialize roles.

They created a dedicated onboarding team responsible only for implementation and setup.

They built specialized resources for reporting and analytics.

And they created different engagement models for smaller accounts versus strategic enterprise customers.

Why?

Because a single CSM simply cannot master every function at a high level.

Specialization allows teams to scale faster and deliver better outcomes for customers.

But most importantly…it frees the CSM to focus on the most valuable part of the role.

Building relationships.

Jim put it perfectly.

Not trying to do every task themselves.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

Book a call to discuss a workshop

In Partnership With

Hey {{first_name | CS Pro}},

Did your team just have an incredible annual kickoff?

Big stage, big vision, big energy. Everyone leaves inspired…and then three months later nothing actually changes.

In this week’s podcast episode, I’m breaking down why that happens and what Customer Success leaders need to do instead if they actually want predictable renewals and upsells.

But first, today’s sponsor

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With Matik, CS teams can:

• Automate QBR creation for every account across your team

• Ensure each QBR tells a consistent, value-focused story

• Scale personalized engagement without adding headcount

The RKO Energy Trap

Let me start by saying this clearly.

I LOVE kickoff season.

January and February are full of SKOs, RKOs, GTM kickoffs… and honestly the energy is contagious. Teams travel somewhere nice, leaders share the big vision for the year, and everyone walks away motivated.

But the Linkedin posts do no share something super important…what happens after?

An annual kickoff is not a revenue strategy.

It is a spark of energy.

Kickoffs create excitement. They align teams on vision. They introduce new frameworks and targets.

But that excitement fades quickly if it is not reinforced.

There is actually a learning concept called the forgetting curve. It shows that without reinforcement people forget up to 70% of what they learned within days.

Days. Not weeks or months….DAYS.

So imagine this. Your company spends months planning an incredible kickoff. The team flies somewhere amazing. Leadership presents new strategies, KPIs, revenue targets, playbooks.

And within a few weeks most of it starts fading.

Not because the strategy was bad.

Because the behavior was never reinforced.

That is the part most teams miss.

Why Behavior Doesn’t Actually Change

Customer Success teams are busy.

Calendars are full. Meetings are stacked back to back. Everyone is juggling customer calls, internal updates, escalations, renewals, and reporting.

When teams are operating in that level of busyness, they default to what feels familiar.

And for many CS teams, the familiar pattern is the check in call.

• You ask how things are going.

• You review product usage.

• You talk about upcoming updates.

• You promise to follow up with an answer to something.

And then the call ends.

Nothing is necessarily wrong with that conversation, but it does not move the account forward in a meaningful way.

During kickoff, leaders often introduce concepts like value storytelling, expansion strategy, or revenue ownership. The intention is to shift the team from reactive support into proactive revenue conversations.

But here is the gap.

Those skills are rarely practiced after kickoff.

Sales teams rehearse constantly. They role play objection handling. They review deals together. They refine their pitch week after week.

Customer Success teams rarely create space for that type of practice.

Instead, the expectation is that CSMs will simply absorb the strategy and execute it during live customer conversations.

That is a huge leap. You cannot just give 120% NRR targets to you team and a playbook and expect them to execute. You are just setting yourself up for failure and disappointment of a playbook is your strategy.

Revenue conversations are a skill. And like any skill, they require repetition to build confidence.

Without repetition, people fall back into the behaviors they already know.

The rhythm that actually builds revenue skills

If you want your team to improve renewals, identify expansion opportunities, and run stronger executive conversations, you need something far more powerful than a once a year kickoff.

You need a monthly enablement rhythm.

This does not have to be complicated.

In fact, the most effective approach is usually the simplest.

Each month your team focuses on one revenue skill.

One topic.

One area of improvement.

And you apply that learning directly to real customer accounts.

For example, one month might focus on forecasting and renewals. The team reviews live accounts together and identifies early risk signals. Managers help CSMs practice how to communicate renewal value clearly.

Another month might focus on white space analysis. The team maps product usage across accounts and identifies areas where the customer could expand.

A different month might focus on ROI storytelling. The team works on connecting product usage to measurable business outcomes so that renewal conversations feel clearer and more confident.

By focusing on one skill at a time, teams can practice it repeatedly. Over time, those conversations start to feel natural.

This is exactly how confidence develops.

Not from hearing something once.

But from practicing it again and again.

Weekly Challenge

Here is something simple I want you to try this week.

Open your calendar.

Block a recurring one hour session each month for the next three months with your Customer Success team.

Then give each session a theme.

Month one could focus on forecasting.

Month two could focus on white space analysis.

Month three could focus on ROI storytelling.

The goal is not to introduce ten new frameworks at once.

The goal is to create repetition.

Because kickoffs create energy.

But repetition is what actually builds revenue.

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

 When was the last time you finished a customer call and thought, that actually moved the account forward?

Not that the customer was happy. Not that everything looked good. But real forward movement.

If that question feels uncomfortable, this episode was for you.

But first, today’s sponsor

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When value is not clearly communicated, competitors step in. CS teams need a scalable way to show impact across every account.

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Why Check in calls are failing you

Customer Success teams are BUSY. Calendars are packed. Meetings are nonstop. Calls are happening weekly, sometimes more.

And yet renewals still feel stressful. Expansions feel awkward. Value feels fuzzy.

That disconnect is not because you are bad at your job. It is because most teams are still running check in calls and calling them value.

Check in calls feel safe. They feel polite. They feel easy to control.

But check in calls are designed to maintain relationships, not grow them.

In 2026, maintaining is not enough.

When budgets tighten and leadership scrutiny increases, relationships alone do not protect renewals. Happy customers still churn when no one can articulate why the product matters to the business.

This is where many CS roles accidentally become reactive. When conversations start with “How are things going?” or “Any blockers?” you hand over control of the agenda. You become an order taker instead of a strategic partner.

And over time, that creates burnout. Firefighting. Last minute surprises.

Customer Success is no longer here to maintain. It is here to drive value and growth. If your conversations do not evolve, your role will not either.

The Most common mistakes CS teams make

There are a few patterns I see over and over again across teams.

First, mistaking activity for impact.

More calls does not equal more value. More meetings does not mean accounts are healthier. Activity is easy to measure. Impact is harder. But measuring volume instead of outcomes gives a false sense of progress.

Second, talking about the product instead of business progress.

Customers do not buy software for dashboards, features, or integrations. They buy outcomes. Time saved. Revenue gained. Risk reduced. Efficiency improved.

The question is not how well they are using your product. The question is how their business is moving forward because of it.

Third, avoiding uncomfortable questions.

CSMs often want to be agreeable and likable. But avoiding hard conversations early creates chaos later.

When priorities shift, when progress stalls, when executives disengage, it is your job to surface that reality. Not to smooth it over.

Finally, failing to anchor conversations to outcomes.

If you cannot clearly articulate what success looks like, how it is measured, and what has been achieved, value becomes invisible. And invisible value is the fastest path to churn.

What value calls actually look like

A value call is not a sales call. It is not pushy. It is not scripted.

It simply has structure.

Every value call should do three things.

First, re-anchor the outcome.

Start the conversation by reminding the customer why they bought. What problem were they trying to solve. What outcome mattered most?

This sets the context for everything that follows.

Second, name the progress.

Progress does not need to be massive. It can be a small step forward. What matters is clarity.

Be explicit about what has moved and what has not. Progress builds confidence. Stagnation creates urgency.

Calling this out positions you as a strategic advisor, not a customer therapist.

Third, define the next value milestone.

If a call ends without a clear next step, value resets to zero. Momentum disappears.

Your customer is busy. You must guide them. What needs to happen next to keep value moving forward?

This is what turns conversations into momentum. And momentum is what eventually leads to expansion, without forcing it.

Weekly Challenge

This week, take ONE upcoming customer call and redesign it as a value call.

Before the meeting, write down:

• The outcome you will anchor at the start

• The progress made since the last conversation

• The next value milestone required to keep growth moving

Go into the call with that structure.

Pay attention to how the energy changes. How the customer engages differently. How the conversation feels clearer and more intentional.

That is what real value feels like in real time.

Customer Success is not about checking in.

That belongs to support.

Customer Success is about moving value forward.

Have a listen to the full podcast:

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

Most revenue success plans do not fail because they are poorly designed. They fail because no one actually uses them. They get built during onboarding, shared in good faith, and then quietly abandoned in a shared drive until renewal panic kicks in.

If you have ever spent hours creating a beautiful success plan, only to realize it has not been opened in months, you are not doing anything wrong. You are experiencing a system problem that almost every CS team has right now.

In today’s world of tighter budgets, leaner teams, and constant pressure to prove ROI, success plans should be one of the most powerful tools a CSM has. Instead, they have become a checkbox exercise. Something we create because we are told to, not because it actually helps us run better customer conversations.

This week’s podcast episode is about changing that. We are talking about how to build a revenue success plan that your customer actually uses. Not a document for internal optics, but a living tool that guides every conversation from onboarding to renewal and makes revenue feel natural instead of awkward.

If success plans feel frustrating, forced, or pointless in your role right now, keep reading. This one is for you.

But first, today’s sponsor

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That's the problem we've been working on at Hook. Activator is our new AI agent that builds a unique path for every customer, adapts in real time, and keeps every action focused on getting them to value. Your team can keep doing what they do best: defining the outcomes that matter, and the agent focuses on getting customers there.

If onboarding at scale is something you're rethinking this year, we'd love to show you what we've built.

Why success plans fail in the real world

Let’s start with a hard truth.

Success plans are not a bad idea. They fail because they are built once, filed away, and never used again.

I’ve made every mistake in the book here. Early in my career, I built what I thought were perfect success plans. Detailed. Structured. Color coded spreadsheets. I rolled them out during onboarding, shared them with customers, and then… never looked at them again.

They quietly died in Google Drive.

The problem was not the template. It was how I treated the plan. I treated it like a document instead of a tool.

Most success plans fail because they are static. They are created for optics, not for decision making. They become a one time onboarding exercise instead of something that guides every customer conversation from kickoff to renewal.

When that happens, renewals feel heavy. Expansion feels awkward. Revenue feels like a last minute ask instead of a natural outcome.

And that is exactly why so many CS teams feel uncomfortable owning revenue today.

The biggest mistakes CSMs make with success plans

The second reason success plans fail is language.

Many plans are written in internal language. Product terms. Feature names. Acronyms that make sense to us but mean nothing to customers.

I used to measure things like number of trainings completed, features launched, dashboards built, even number of QBRs delivered. None of those things are outcomes. They are activity.

Activity does not equal value.

Customers do not renew because they attended three trainings. They renew because something in their business improved. Revenue grew. Time was saved. Risk was reduced. Speed increased.

Another mistake I made was building the plan for the customer instead of with them. I thought I was being helpful by doing the work upfront. In reality, I robbed them of ownership.

If your customer did not help define success, they will never feel accountable to it. A success plan only works when it is co created.

And finally, many plans track what happened instead of what is changing. They look backward instead of forward. A good plan does not need perfection. It needs direction.

What will look different in 30, 60, or 90 days if this partnership is working?

If your plan cannot answer that, revenue will always feel forced.

What actually works, the revenue success plan

This is where the shift happens.

A revenue success plan is not a document. It is a shared operating system between you and your customer.

It has three core elements.

First, clear business outcomes. Not what the customer wants to do, but what they want to achieve. Revenue growth. Cost reduction. Time savings. Risk mitigation. Speed to market. Outcomes anchor the entire relationship.

Second, metrics that show directional progress. Not perfect graphs, but proof of movement. What is changing over time because your product exists in their business?

Third, a living narrative. What moved forward. What is blocked. What is at risk. This is what makes revenue conversations feel normal because you are already talking about impact every step of the way.

When this plan is set up correctly, it does the heavy lifting. Renewals and upsells stop feeling like sales conversations. They become logical next steps.

I use revenue success plans everywhere. Onboarding to set expectations. Adoption to keep focus. Business reviews to tell a clear story of value. Expansion to map outcomes to solutions.

When a customer asks to do everything at once, the plan becomes your anchor. What matters most right now based on the outcomes we agreed to?

That is how you move from reactive to strategic.

The biggest takeaway I want you to remember is this.

A revenue success plan only works when it is outcome focused, co created, and used continuously. It is not a renewal tool. It is a relationship tool.

This entire framework, including plug and play templates and real customer examples, is something I teach step by step inside RevUp Academy. It is how CSMs stop winging revenue conversations and start leading them with confidence.

If this episode helped you, share it with a CS friend who is tired of building success plans that go nowhere.

And as always, thank you for being here. I’ll see you next week.

Have a listen to the full podcast:

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

 Let’s talk about the question every CS team is being asked right now.

How do you prove ROI when your product does not clearly show it?

If you have ever walked into a QBR or renewal knowing the value is there, but struggling to put it into executive language, you are not alone. Dashboards fall short. Metrics feel incomplete. And suddenly all the pressure is on you to justify the relationship.

This week’s episode tackles that exact challenge. I sat down with Natasha Evans, VP of Customer Growth at Hook, to break down how CS teams can communicate real, credible value even when the product is not doing the storytelling for you.

But first, today’s sponsor

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• Renewal deck template

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Why ROI Feels So Hard Right Now

One of the biggest themes from this conversation was something I see every single week.

CS teams are being asked to prove ROI, but their product does not do the storytelling for them.

Dashboards are incomplete. Metrics are fuzzy. And customers are overwhelmed with tools that all claim to save time, money, or effort.

Natasha was very honest about this. Most products do not hand you a clean ROI number. And waiting for perfect data is one of the fastest ways to lose momentum with customers.

The shift we talked about is simple but uncomfortable.

Stop waiting for your product to save you.

Value does not start in dashboards. It starts in conversations. It starts with setting the tone from day one that your role is to understand business outcomes, not just deliver features.

If you do not anchor your relationship around outcomes early, you will get pulled into delivery mode forever.

How to Build a Value Story Without Perfect Data

One of my favorite parts of this episode was how practical Natasha got about ROI.

ROI does not have to be complex. It does not have to be perfect. And it definitely does not have to be scary.

At SalesLoft, her team built simple value narratives around things they could actually measure. Activities. Usage patterns. Time saved.

They focused on a small set of actions inside the product and assigned conservative time estimates to each one. Nothing inflated. Nothing exaggerated.

Then they told a clear story.

Because your team did X this many times, here is the estimated time saved. That time either reduced workload, avoided headcount, or unlocked more productivity.

For some customers, the time saved was enough. For others, that time could be translated into revenue impact.

And here is the key part.

They socialised these estimates with champions before ever taking them to executives.

That one step alone builds trust and avoids awkward pushback later.

What Strong Value Conversations Look Like From Day One

Another big takeaway was how early value conversations need to start.

Strong value articulation does not begin at renewal. It begins in your very first interaction.

Natasha shared something powerful. Before you ask big questions, you need to explain why you are asking them.

Tell your customer you want to understand what will make them look good internally. Tell them you want to measure success together so you can prove the value of the work you are about to do.

That context changes everything.

From there, you anchor on business objectives. Not product adoption. Not usage for the sake of usage.

Business outcomes.

And when the person you are speaking to cannot answer those questions, you adjust. You ask about company priorities, leadership messaging, or what the CEO talks about at all hands.

Value conversations are not about asking harder questions. They are about asking smarter ones, to the right people, at the right time.

If this episode resonated with you, share it with a fellow CS Pro who is tired of fighting the ROI battle alone.

Have a listen to the full podcast:

Watch on YouTube

Listen on Spotify

Listen on Apple

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

 Let me ask you a question that might make you uncomfortable.

If Customer Success disappeared tomorrow… would your company replace it with Account Management or Support?

Because in 2026, that question is no longer theoretical. It is already happening. CS teams are being absorbed into Sales or pushed closer to Support, with the same title but a very different job.

In this episode, I break down why this is happening, the mistakes that quietly got us here, and the ONE decision that determines where Customer Success actually lands next.

Because if you do not define Customer Success for yourself, someone else will.

But first, today’s sponsor

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• A quiz to grade your current QBRs

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This ebook is brought to you by Matik - Automate presentations, documents, and reports directly from your data, powered by AI you can trust.

Why CS Is Under Pressure Right Now

Customer Success is not being removed.

It is being re evaluated.

Budgets are tighter than they were a few years ago. Teams are leaner. And leadership is asking every department the same question, even if they are not saying it out loud.

How does this role make or save money for the business?

For a long time, CS could answer that question loosely. Good relationships. Happy customers. Strong usage. That was enough.

It is not enough anymore.

When a function cannot clearly explain how its work connects to revenue or risk reduction, leadership starts to simplify it. If your day to day work touches renewals or expansion, it gets labeled Account Management. If your time is spent on issues, adoption, and reactive requests, it gets labeled Support.

Not because CS is not valuable.

Because ambiguity does not survive pressure.

And Customer Success has been ambiguous for a long time.

The Habits That Are Hurting CS

1️⃣ We equated value with activity.

Calls. QBRs. Check ins. Emails. Meetings.

Busy looks productive. But more activity does not automatically mean more impact. And it definitely does not translate to revenue in an exec conversation.

2️⃣ Waiting until renewals to talk about value.

So many CS teams save impact for the big QBR or renewal deck. By then, you are already too late. Customers want value reinforced in small moments, consistently… not one giant presentation at the end.

3️⃣ Avoiding revenue language.

I see this constantly. CSMs saying “I do not want to sound salesy” or “that is not my job.”

Silence does not protect you.

Avoiding commercial conversations does not save your role.

It makes it easier to remove.

4️⃣ Letting other teams tell your story.

Sales will happily take credit for expansion. Finance will reduce you to cost. Support will frame value through tickets.

If you do not articulate your impact, someone else will. And their version will not serve Customer Success.

What Actually Protects the Role

At the end of the day, the future of CS comes down to one thing.

Can you clearly connect customer outcomes to business outcomes?

When you can explain how adoption protects revenue.

How progress creates expansion readiness.

How outcomes align to executive priorities.

That is when CS becomes a growth function, not a cost line.

This starts with defining success in the customer’s language, not your product’s language. Tracking progress visibly, not just internally. And treating revenue conversations as part of success, not something awkward or uncomfortable.

Talking about renewals or upsells is only uncomfortable when value has not been clearly shown. This is not about turning CS into Sales. It is about making the value of your work impossible to ignore.

Weekly Challenge From the Podcast

Here is what I want you to do this week.

For each of your accounts, write one sentence:

Because of our work, this customer is now able to ______.

If that sentence feels hard to write, that is useful information. It means your work may be drifting into activity instead of impact, and that is exactly where your focus needs to shift.

Customer Success is not disappearing in 2026.

But unclear Customer Success is.

Have a listen to the full podcast:

Watch on YouTube

Listen on Spotify

Listen on Apple

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

 If your company is moving upmarket and your CS team still runs like a high-volume machine, this episode is basically a mirror. Alon Ahronberg, VP of Customer Success at Atera, breaks down what actually changes when you shift from product-led growth to sales-led growth.

If your GTM team is moving upmarket than this week’s episode is perfect for you. Alon shares tons of practical tips, tricks and best practices on how to make your entire company work differently as you start to serve a new segment of customers.

But first, today’s sponsor

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Hook's Success Planner will even flag when you haven't identified business-level objectives, and coach you towards defining goals that are actually worth aligning to. No sugar-coating, just clear, actionable insights for CS-led impact.

Built for busy CSMs who want to save time and level-up how they plan for success, because helping CSMs genuinely matters to us.

Why “just hire more CSMs” is the trap

One of the biggest callouts Alon makes is the mistake leaders default to when the business starts going upmarket: doing the same thing, just with more people.

It sounds logical at first. More customers, bigger deals, higher expectations, so you hire more CSMs. The problem is the motion has changed, and your operating system has not.

At Atera, they had tens of thousands of customers, and a CS org that was still built for scale. CSMs were managing books like 1,000 accounts, sometimes 500. That can work in a product led motion where the product does most of the heavy lifting, and CS is largely reactive, responding when something breaks, when a customer complains, when someone asks for help.

But as sales led revenue grew, Alon mentioned it was already close to 40% of revenue coming from sales. That shift brought in bigger organizations, bigger deals, and a totally different service expectation. The CS org was lagging behind, not because the team was not good, but because the model was wrong for the new customer type.

So the first shift was not “work harder.” It was “redesign how we serve.”

The rebuild starts with segmentation, health, and QBR tools

When you have an existing team and a massive customer base, you cannot flip a switch and expect everyone to suddenly run perfect customer journeys. Alon was really clear on this, it has to be one step at a time, and you have to give the team tools.

Here is what he prioritized early:

1. Redraw the book of business

   You have to draw a line between no touch accounts and managed accounts. At the beginning, their easiest starting point was ARR and account size, with a few exceptions. Later, they started refining segmentation further, including organizational size.

This matters because your “managed account” motion should not feel like a scaled support motion. It should feel intentional, proactive, and value led.

2. Define a health score, even a simple one

   They started by mapping accounts and defining what “healthy,” “neutral,” and “at risk” actually means. Even if it is imperfect at first, even if part of it is CSM sentiment, it creates a shared language and a baseline view of the portfolio.

3. Standardize QBRs, because the team needs structure

   They built QBR formats for bigger accounts and mid touch accounts. The point was not to create a pretty deck. The point was to help CSMs ask better questions, gather better data, and then use that data to strengthen health scoring and proactive planning.

4. Add forecasting so you can operate strategically

   They introduced a forecasting mechanism to understand where they would land in upcoming quarters, where risks were sitting, and how to move before things turn into fires.

The theme across all of this is simple: get out of reactive mode by creating a system the team can actually execute.

Adoption is not “use the product,” it is “use what drives renewals”

When I asked Alon to define adoption, I loved that he did not pretend it was easy. Their product is a platform with multiple pillars, and adoption is always evolving depending on customer maturity, use case, and what is new in the product.

What they did was map the platform into pillars, then identify the “sticky” features inside each pillar, the ones most tied to value and longer term retention. They looked at things like usage volume per account, license utilization, and feature usage patterns, then built a picture of what “healthy usage” looks like.

But here is the important nuance: they still anchor it in conversation. Not every product area is relevant for every customer, so success plans have to be tailored. Adoption is not a universal checklist, it is a focused plan tied to customer outcomes.

They are also experimenting with using AI and conversation intelligence to speed up insights. The goal is to move from manual dashboards toward smarter recommendations, including eventually pushing personalized recommendations to end users, not just champions. Right now it is still in experimentation, but the direction is clear: reduce friction for the team, and make value visibility more automatic.

And then there is the part that most teams skip: re onboarding.

Alon’s team rebuilt onboarding into clear packages based on customer size and complexity, with explicit goals, checklists, and a clear success definition. Then they realized something big: they had a large population of strategic accounts that never went through a proper onboarding experience.

So they proactively launched a re-onboarding initiative, before customers complained.

They identified the population, reviewed usage and gaps, and approached customers with a clear “what’s in it for you” offer. The message was basically: we noticed underutilized areas, we can assign a professional services engineer to help you implement and get more value. They pulled in extra support to operationalize it, including people from presales and tier two engineering, and called the task force “Delta Force.”

This is such an underrated lesson. Re-onboarding is not an apology tour. It is a proactive risk mitigation play, and it can be framed as additional value.

If your company is moving upmarket, check out the full episode for more tips. Keep it simple, keep it fast, and focus on momentum.

Have a listen to the full podcast:

Watch on YouTube

Listen on Spotify

Listen on Apple

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika

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Hey {{first_name | CS Pro}},

Renewals don’t become stressful at the end, they are decided months earlier. In this episode, Emma Lampert breaks down how to stop “hoping” your forecast is right, and start building a renewal and expansion system you can actually trust.

But first, today’s sponsor

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Are you joining the Revenue Party happening in a few hours?

Join me for a BRAND NEW live masterclass session where I will walk you through the framework I use to help CSMs move from check in calls to outcome led conversations that customers actually value.

In this masterclass, you will learn how to:

• Shift from activity driven check ins to outcome focused conversations

• Clearly show value in every customer interaction, even without a perfect product

• Build momentum toward renewals and expansion instead of scrambling at the last minute

This is the foundation for predictable renewals, stronger customer relationships, and more strategic influence as a CSM.

Join live and learn how to start driving revenue, not just managing accounts.

⏰ Wednesday, January 28th at 10 am PT / 1pm ET / 6pm UK

🔗 Save your spot now: thecustomersuccesspro.com/masterclass

Commercial is not a dirty word

Emma says it plainly, customer success IS commercial. Not because you are pushing product, but because renewals are a lagging outcome of the value you delivered all year. If the customer got real outcomes, you protect the renewal. If they did not, you either go flat or you lose it.

I loved the way she reframed it…CS is still advisory, still strategic, still about outcomes. But it’s advisory with a purpose. You are helping customers win, AND you are responsible for the revenue that comes from that customer staying and growing.

One of the biggest reasons CS teams struggle with revenue ownership is detachment. Emma called it out… too many CSMs do not understand how their work ties to the way the business makes money.

Her advice was simple and honestly, a little uncomfortable (in the best way)…

That means understanding how your company generates revenue, how costs show up, and what happens downstream when you give discounts, credits, or concessions. If you do not understand your company’s P and L, talk to your finance leader and learn it.

Because this is the truth…you cannot lead a commercial function if you do not understand the commercial model.

Quota is just math, stop panicking

The moment Emma said her team has a 120% NRR target, I smiled… because yes, that’s a quota. Call it a KPI if you want, but it is still a number you are accountable to.

What makes Emma’s approach work is that she does not throw a scary target at her team and hope activity magically turns into revenue. She reverse engineers it.

Here’s the mindset shift she teaches:

If your book is $1M and your target is 120% NRR, the “extra” you need is $200k. Break it down by quarter. Then break it down by average expansion size. Then turn it into the number of real opportunities you need in the pipeline.

Suddenly “we need $200k” becomes “we need two real expansion motions this quarter” or “we need a pipeline of X projects that will drive adoption and usage.”

That’s when quota stops feeling like pressure and starts feeling like a plan.

She also made a point that a lot of CS leaders forget… CS has an advantage sales does not. Sales has to create a pipeline from scratch. CS already has built-in revenue events on the calendar…renewals.

So instead of treating renewals like random calendar admin, she recommends timeline mapping. Look at the year, find your biggest renewals, and build your expansion and value plan around them months in advance.

That’s how you make revenue repeatable. Not by doing more calls, but by engineering the right moments.

The renewal system that builds forecasting confidence

This is the part I think every CS leader listening needs to steal.

Emma forecasts six months out, she looks at the current quarter and the next quarter. The reason is simple…you need runway. If you find risk three months out, you cannot do much. Customers are busy, meetings take time to book, and priorities shift. Six months gives you space to actually change the story.

At the six-month mark, the CSM needs to have an explicit conversation with their champion about whether enough value has been delivered to justify another year. Not vibes, not usage alone, not “I think they like us”… an actual conversation.

And then she layers in her three-question framework to keep account planning focused on what actually predicts outcomes:

1. WHO CARES

Who are your stakeholders, who is engaged, who signs contracts, are you truly multithreaded, do you have champions AND decision makers?

2. HOW DEEP

How embedded are you, surface level usage or integrated workflows, one product or multiple, how sticky is your footprint?

3. WHAT ROI CAN THEY PROVE

Can the customer actually talk about the ROI, do they have a defined outcome, what is changing over time?

Notice what she is NOT doing…she is not obsessing over “health scoring” as a data collection exercise that no one uses. This is more like a practical pulse check that forces the right conversations.

Then comes the cadence…weekly forecast calls.

Every week, the team updates the forecast in HubSpot, including best case, worst case, and notes on what changed.

Emma’s take was savage but accurate… “Nothing changes week to week because you are not focused on it.”

The moment forecasting becomes a weekly rhythm, it stops being a last minute scramble.

And when it comes to best case and worst case, she ties it to evidence, not hope. In her consumption model, usage is a leading indicator of revenue. In traditional SaaS, the parallel is seat utilization or feature adoption. If they bought 100 seats and only 10 are used, your worst case is not 100 seats. You need to be honest.

One more moment I think every CSM needs to hear… direct questions are your friend.

Emma shared a churn story where she relied on “usage and vibes” and got blindsided. The real issue was the value did not stack up for the true long term owner.

Her point was simple… if they are not going to renew, they are not going to renew anyway. Asking earlier helps everyone. Your customer does not want a last minute awkward conversation either.

Now on upsells… her approach is not “show up three weeks before renewal and ask for more money.” Instead, she sees upsell as the natural result of consistent discovery. Discovery is not a kickoff activity, it is an every call habit.

If you are aligned to their roadmap, if you ask enough questions, if you let them sit in the pain long enough to understand impact, expansion becomes “how else can we help” instead of “how can we sell more.”

That’s it for this week. If you want to hear the full conversation with Emma (especially her forecasting cadence, the quota breakdown, and her take on outcome economy), go listen to the episode and tell me what hit home for you.

Have a listen to the full podcast:

Watch on YouTube

Listen on Spotify

Listen on Apple

I hope you enjoyed this week’s newsletter.

If you have any questions or suggestions, please feel free to contact us.

Cheers to your CS success,

Anika