Feature Story
Let me ask you something.
When was the last time you sat down with a customer, not for a QBR, not for a renewal conversation, not because a cadence told you to, but just to understand who they are, how they actually work, and what they genuinely need from you?
If you had to think about that for more than a second, keep reading.
Here's what I see when I look at most CS organizations right now. And I'm not saying this to be harsh, I'm saying it because it's true, and because most people in this industry are too polite to say it out loud.
You have a 90-day onboarding program that was never built around how your customers actually work. It was built around what felt like a reasonable timeline internally or because someone told you that was the magic day count to hit value realization. Your customers are just along for the ride.
You're running QBRs because that's what CS teams do. Not because your customers asked for them and not because they're consistently driving value. Because they're on the calendar and they signal that you're engaged. In fact most teams don’t engage their customers outside of these meetings.
You sent an NPS survey and called it feedback. A number on a scale of one to ten does not tell you why a customer is struggling. It doesn't tell you what they're not saying. It tells you how they felt in the moment they clicked the link. And honestly the percentage of customers who actually complete the survey does not give you enough data anyway.
You built a health score that was easy to create, not one that tells the truth. Green doesn't always mean healthy. Sometimes green means nobody looked closely enough. In fact, I see teams just sitting on explosive watermelon accounts. The ones that are green on the outside and red on the inside … churn, just waiting to happen.
You hired an Onboarding Manager, a CSM, and an AM because that's the structure you've seen everywhere. Not because you pressure-tested whether that's the right model for your customers at your stage. In fact I’ve met with teams who didn’t need a CSM function at all.
You bought a CS platform before you had a strategy. And now your strategy is whatever the platform makes easy to do. You don’t have to use all of the features in your CSP if it doesn’t support your strategy … I don’t care what your CSP CSM says.
You segment customers by ARR because it's simple and clean. But what a customer spends has nothing to do with what they need. A $10K customer with deep complexity deserves thoughtful support. A $200K customer who's simple to serve doesn't need your most senior CSM.
You're implementing AI because everyone else is. Not because you've identified a specific problem it solves. Not because you've tested whether it actually improves outcomes. Because it's the thing to do right now.
I want you to sit with that list for a minute. Not defensively. Just honestly.
How many of those things are true in your organization right now?
Because here's what I know from the inside of this work. I was not exempt from any of it.
My first CS leadership role was not really mine. I stepped into a strategy someone else had built, and I inherited a program that was already in motion. We scaled from $20M to nearly $100M in ARR, and I watched what worked and I took notes.
My second role looked a lot like the first. Again, this wasn’t mine but I saw a similar structure, similar motions, similar outcomes, and so I kept believing. I thought: this is the playbook. This is how you do Customer Success.
Then came my third role. And this time, I was building it alone.
I didn’t inherit a pre-built structure. There was no existing motions to follow. Just me, a blank slate, and a team looking for direction. And what did I do? I went straight back to the playbook I'd been trusting, and it didn't fit.
The customers were different, the product was different and the way people needed to be supported was different. Every time I tried to force the standard motion, something felt off. The QBRs felt performative, health scores weren't telling the truth and the onboarding timeline wasn't built for anyone's actual reality. It was built for mine.
That's when it finally clicked.
There was never a universal playbook. What I'd seen work in those first two roles worked because it was built for those customers, in that context, at that moment in time. It wasn't transferable, it was contextually correct. And I had mistaken context for truth.
The only truth I found, the one I now build everything around, is this: the only Customer Success program that actually works is one that is built for and with your customers. Not for your internal reporting, not around your technology and not because it's what the industry says CS looks like.
For your customers. That's the whole thing.
So what does that actually look like in practice?
→ It looks like interviewing your customers to understand who they are and how they work before you design anything.
→ It looks like helping them define what success means for them, even if that takes more than one conversation.
→ It looks like building onboarding around their reality, not your timeline. It looks like showing up to every touchpoint prepared, with real insights and genuine intention, not just to check a cadence box.
→ It looks like telling the story of progress early and often, not saving wins for the end of the quarter when it's convenient for your renewal cycle.
→ It looks like having honest conversations with executives when something actually matters, not when the calendar tells you to.
→ It looks like collecting real feedback, sitting in the discomfort of what customers aren't saying in a survey, and having those harder conversations.
→ It looks like building for customer outcomes so completely that if you stripped away all your internal metrics, you'd still do the work the same way.
And it looks like stopping the technology shopping until you know what problem you're solving.
The Takeaway: The question is not "what does a good CS program look like?" The question is "what does success actually look like for my customers?" Let that answer build your program. Everything else is just performance.
THE RESOURCE
Is Your CS Program Actually Working? An Objectives Checklist
Before you audit your motions, audit your objectives. Here's a checklist to help you assess whether your CS program is grounded in the right foundations. Be honest with yourself.
Customer Understanding
We have documented what success means for each customer segment, not just their ARR tier
We regularly interview customers to understand how they work, not just whether they're happy
We can clearly articulate the outcomes our customers are trying to achieve
Program Design
Our onboarding is designed around how our customers actually operate, not a default timeline
Our segmentation reflects customer needs and complexity, not just what they pay
Our technology supports our strategy; our strategy was not built around our technology
Engagement Quality
Every customer touchpoint has a defined purpose and delivers something of real value for the customer, not your internal team
We socialize customer wins and progress on an ongoing basis, not just at renewal
We have executive relationships built on trust, not just contract cycles
Measurement
We measure what is predictive of customer outcomes, not just what is easy to pull
Our health scores reflect the truth, even when the truth is uncomfortable
We collect qualitative feedback beyond surveys and act on what we hear
Honest Assessment
Our CS program is designed to serve our customers' outcomes first
If we stripped away all internal reporting, we would still do this work the same way
If you're checking fewer than ten of these, you're not running Customer Success, you're performing it.
But the good news is: that can change.
AI IN CS
Here's the irony of the current AI moment in Customer Success: we're using it to do more of the wrong things, faster.
Automated health scores that still measure the wrong signals, AI-generated QBR summaries for meetings that shouldn't exist, scaled outreach that reaches more customers with less value and efficiency layered on top of broken motions isn't progress. It's just faster drift.
The CS teams getting real value from AI right now are using it to do things that were previously impossible at scale, not to automate what was already broken. They're using AI to synthesize customer conversations and surface patterns in feedback that a human would miss across hundreds of accounts. They're using it to help CSMs prep for calls with actual context: recent product activity, support history, relevant signals, so they can show up with intention instead of just showing up. They're using it to flag early risk that lives outside the health score.
AI is most powerful in CS when it makes your team smarter, not just faster.
Before you automate anything, ask whether it's worth doing at all. Because scaling a broken motion just means you're breaking more things, more efficiently.
PODCASTS
The Accountant turned Chief Marketing & AI Officer at 2X featuring Lisa Cole
From retail cell phone sales to Chief Marketing & AI Officer, Lisa Cole's 25-year career was shaped by one recurring problem: marketing wasn't being taken seriously. She joins the show to talk reinvention, leadership, AI, and what it actually looks like when marketing becomes a company's primary growth driver.
EPS 9: Show Me the Money - CS Leader Edition
You're managing millions in revenue and still begging for budget. Kristi and Rafaella Fontes get real about why CS leaders lose the resource conversation every time, and what the structural dysfunction keeping CS underfunded actually looks like.
THE SERVICES
I work with CS leaders and organizations who are serious about getting Customer Success right.
Advisory
Strategic partnership for CS leaders who need a thought partner, not another framework.
Coaching
1:1 coaching for CS professionals who are ready to lead with more clarity and confidence.
Education & enablement
Workshops and programs built for teams who want to level up, not just check a box.
Speaking
Keynotes and sessions that challenge how your audience thinks about Customer Success.
THE QUESTION
When you look at your CS program honestly, what's the one thing that exists because it's always been done, not because it's actually working?
Reply and tell me. I read every one.
A FINAL NOTE
CLOSING WITH KRISTI
I'm not writing this to make anyone feel bad about where their program is today. Most of us inherited something, or built something under pressure, with limited resources and unrealistic expectations. That's real, and I respect it.
But the industry keeps asking why CS struggles to prove its value. Why CSMs are burning out. Why retention is harder than it should be. And the answer is sitting right here. We built programs that look like Customer Success instead of ones that actually do it.
You don't need a new tool, you need a clearer truth. Start there.
If this landed for you, let me know. And if you want to dig into what this looks like in your org specifically, you know where to find me. I’d love to help.
See you next week,
Customer Success. Revenue Follows.