Feature Story
Across my five CS leadership roles I held, a pattern kept showing up that I couldn't ignore.
Onboarding always worked, probably because both sides understood it. There was a start, a middle, and an end. But the moment onboarding closed? The journey started to fall apart.
All of a sudden, customers had their own priorities, budget pressure hit, leadership changed, and a new business unit we'd never met suddenly had opinions about the platform.
And every time this happened, we'd scramble to "augment" our journey to fit their reality, while still trying to force the account into the stage it was supposed to occupy.
It was to satisfy our internal tracking needs and it was a lie.
The moment it fully clicked was in a regular team meeting, reviewing accounts across our book of business. We were going through the usual process and something felt off. The data said things were fine and the stages said customers were progressing. But when we started asking harder questions, we realized the way we were tracking customers was actually hiding risk. Accounts that looked healthy on paper were silently drifting.
Here's what the customer journey model couldn't handle:
When a new executive came into one of our accounts, we had to reorient around their goals entirely. The milestones the previous leader cared about? Potentially irrelevant now. But our journey said the account was in "Growth." It wasn't. It was back at the beginning in everything that mattered.
When we had multiple business units inside a single account, different teams were at completely different points. The account as a whole didn't live in any stage cleanly. Forcing it to was a mess.
When a customer purchased a new product, they were technically back in onboarding while another part of their account was approaching renewal. The journey had no answer for that.
The stage was always fiction and we were just slow to admit it.
So we stopped asking "what stage is this customer in?" and started asking "what milestones have they actually hit?"
This was not about internal actions and not about tasks our team completed. This was now watching behavioral signals and provided evidence that the customer was on a path to real value.
Are they clear on their goals? Is the platform configured to support those goals? Are the right people in it? Can they connect your solution to a business outcome? Is it part of how they actually work?
Those questions don't fit on a timeline. Some customers hit milestone seven before milestone four. Some circle back to milestone one after a leadership change. That's not a failure of the model, that's the model working.
When we made the switch, something shifted immediately. The accounts we thought were healthy looked different. The accounts we thought were risky looked different. For the first time, we could actually see what was happening instead of what the journey told us was supposed to be happening. These milestones and out ability to track them actually became a better barometer of health than any silly health score we ever created.
The Takeaway: Stages tell you where a customer sits in your process, but milestones tell you whether they're actually getting value. Only one of those predicts renewal likelihood and it’s not what you have in place today.
THE RESOURCE
If you're a CS leader or CSM, determine which milestones signal that your customers are on track.
This week I want to point you to the 10 milestone signals I use to evaluate whether a customer is actually progressing toward value, pulled directly from the LinkedIn post that sparked this issue.
Mind you, these are generic so think about your business, your product and your customers and design the milestones that make sense for you.
These are intentionally generic.
I'd encourage you to use them as a starting audit:
Pull up five accounts from your current book of business. For each one, answer the 10 questions honestly. Not based on what your CRM says. Based on what you actually know.
How many can you answer with confidence? How many expose gaps you didn't realize were there?
Are they clear on their goals and what they expect from your solution?
Is their platform configured in a way that reflects those goals?
Are they using the product in ways that lead to success, not just logging in?
Are the right people in the platform, not just licensed?
Do multiple stakeholders understand the value it's driving for the business?
Can they connect your solution to their outcomes, directly or indirectly?
Is your solution part of how they actually work every day?
Is it integrated with the other tools and systems that support how their data flows?
Do they see new use cases as their business evolves?
Does the investment still make sense for them now and into the future?
AI in CS
Milestone Detection
Here's where this gets interesting for CS teams using AI right now.
Most AI-powered health scores are built on top of the same broken foundation: stages, activity data, and login frequency. If the underlying model doesn't reflect actual customer progress toward value, layering AI on top of it doesn't make it smarter. It just makes the blind spots faster.
What milestone-based tracking unlocks for AI is signal quality. When your milestones are behavioral, not operational, you're feeding AI real leading indicators instead of noise.
A few ways teams are starting to use this:
Milestone gap detection. AI flags customers that have stalled between specific milestones, so CSMs can intervene before the customer even realizes they're stuck.
Leadership change alerts. Integrating CRM signals with CS platforms to surface when new contacts are added or executive-level stakeholders change, triggering a milestone reassessment automatically.
Usage pattern analysis tied to milestones. Instead of tracking logins, AI maps user behavior to the milestone it supports. Are they using the features that correspond to their stated goals? That's a real signal.
The goal isn't to automate your CS motion. It's to make sure the motion you've built is actually tracking something real. AI can accelerate that, but only if the foundation is right.
FROM MY WORLD
Quick updates … Events, podcasts, awards, news, etc.
EPS #8: Survive or Thrive: The Real Cost of Lazy CSM Onboarding
Most companies spend months recruiting top CS talent then then hand them a laptop, a Salesforce login and wish them the best.
The National Geographic photographer turned Founder at Verbatim ft. Brianna Doe
She dreamed of shooting wildlife for National Geographic. Instead, she built a top-ranked influencer marketing agency from scratch. In this episode, Brianna Doe, founder and CEO of Verbatim, gets raw about burnout cycles, getting laid off, and the career coach call that changed everything.
NEW CUSTOMER SUCCESS COURSE
The CS Architect Workshop is closing this week and we only have a few spots left.
If you're building a CS program for the first time or finally ready to stop patching the one you have, this is for you.
Over 10 weeks, in a small cohort setting, we build together. Not theory. Not slides you'll never open again. Actual frameworks, real feedback, and a program you walk away with.
Here's what we cover:
How to create customer segments that actually matter (not just sorted by ARR)
How to design an intentional, outside-in customer journey instead of one built around your internal convenience
How to define what a healthy customer looks like in YOUR business, not someone else's benchmark
And so much more
You'll leave with a playbook, a clearer strategy, and the confidence to lead it.
10 weeks. Small cohort. I teach and build alongside you.
Investment: $4,000
We close this week and seats are almost gone. If you've been waiting for the right time, this is it.
👉 Grab your spot here
POLL
When your team reviews accounts, what are you actually reviewing?
A FINAL NOTE
CLOSING WITH KRISTI
The journey you built isn't worthless. But if it's telling you customers are on track when they're quietly disengaging, the map is the problem, not the territory.
Milestones won't fix everything. But they'll show you what's real. And in this environment, knowing what's real is the only competitive advantage that actually holds.
More on this soon. There's a lot more to unpack here.
And if you haven't checked out After the Close yet, this is exactly the kind of thing we get into on the podcast. Give it a listen.
See you next week,
Customer Success. Revenue Follows.