Retention & churn diagnostics
I help companies diagnose and prevent the churn that matters.
If retention is moving in the wrong direction, I figure out why good-fit customers are leaving. If retention is healthy, I find the risks that could change that before they show up in your churn numbers.
- 15+ years of operating experience
- Customer value, retention and growth
- Proven leader
- Early-stage through enterprise
- Fresh, informed outside perspective
- Diagnostic-focused
The problem
Customer retention is harder than it used to be.
A lot of companies are feeling this right now. The product is better. The customer experience is better. Teams have more data and better tools. And somehow churn is still up.
Part of the answer is simply that the ground moved. Companies acquired a lot of customers in 2020–2022 who may never have been a great fit. Budgets are tighter. Buyers are more discerning. AI is changing how work gets done and, in some cases, eliminating the job a product was hired to do altogether. Customers who aren't getting real, meaningful value don't stick around anymore.
Even in this environment, there is still real work to be done, and real retention to be won back.
A real churn problem can take 12–18 months to turn around.
You have to figure out what's causing it, fix the underlying issues, get new and current customers through the improved experience, and then wait long enough for that improvement to show up in a lagging retention metric.
Which is why the best time to solve a churn problem is often before it becomes one.
Not all churn requires the same response.
Some churn tells you something about who you sold to, the market, or how customer needs have changed. Other churn is coming from good-fit customers who should be getting meaningful value from what you sell — and aren't staying.
Both matter. But they don't mean the same thing, and they shouldn't trigger the same response.
All churn hits your retention number, your forecast, the value of the company, and the story leadership has to tell the board. But the first job isn't to try to prevent every customer from leaving. It's to understand which churn you're dealing with, what's actually causing it, and where intervention can make a difference.
Two ways to use the work
Same diagnostic discipline. Two different starting points.
Companies bring me in for one of two reasons: churn has already shown up and leadership needs to understand why, or churn hasn't shown up yet and they want to pressure-test whether customers are actually being set up to stay.
Work backward from customer loss
Churn Diagnostic
You have a churn problem. Let's figure out why.
Maybe GRR or NRR has been declining. Maybe the board is asking questions. Maybe leadership has four theories. Maybe you've already launched a few tactical retention initiatives and nothing seems to be moving the number.
We start by separating churn that warrants operational intervention from churn that's telling you something else — about ICP, historical selling, the market, the product, or how customer needs have changed.
Then we go deep on the churn that matters most: customers who should reasonably be getting meaningful value from what you sell, and aren't staying.
- Which customers are leaving?
- Which losses matter most?
- What patterns explain why good-fit customers aren't staying?
- Where did the experience break, and what changed?
- What should you actually fix first?
Work forward from customer value
Retention Readiness Diagnostic
You don't have a churn problem. Let's keep it that way.
Retention is a lagging indicator. By the time a customer churns, the thing that caused it may have happened months earlier — and you're now 12–18 months from fixing it.
That gap matters most when the business is changing: growing fast, moving upmarket, larger ACVs, more complex customers, a shifting ICP, a new product or service model, more teams involved in delivering value, or a customer base that grew very quickly in 2020–2022.
So instead of starting from the customers you lost, we start from the customers you're selling today and test whether they're actually set up to stay.
- Do these customers get meaningful value?
- Do they get it quickly?
- Do they know they got it?
- Do the people making the renewal decision see it?
- Do they keep getting value as their needs change?
Two starting points, two investigations
Two starting points: work backward from customer loss, or forward from customer value.
Churn Diagnostic
Working backward from customer loss
01
Get specific about the churn we're trying to understand
The overall retention number tells us there's a problem. It doesn't tell us what the problem is. We start by understanding who is leaving, what kinds of customers they are, when they're leaving, and which losses deserve a closer look — particularly good-fit customers who should have been getting meaningful value.
The goal isn't to decide upfront which churn was preventable. It's to get specific about the losses we're trying to understand.
02
Get the full story behind why they left
Then we talk to the people who saw different pieces of what happened: executives, managers, frontline teams, and, whenever possible, customers — including former customers.
Leadership has one version. The people closest to the customer often have another. And the customer may tell us something neither group has heard before.
Can we do this without customer interviews? Yes. Is the work better when I can talk to your customers? Also yes. Whenever possible, they're part of the process.
03
Pressure-test what we're hearing
Conversations surface patterns and hypotheses. Then we use the information you already have — retention data, customer history, usage or engagement signals, onboarding timelines, support history, or whatever else is relevant — to see what holds up.
The goal isn't to build a perfect model. It's to distinguish an anecdote from a pattern and get confident enough about the causes to act.
04
Prioritize what actually needs to change
We separate symptoms from causes and narrow the work to the few things that matter most.
You'll know what I believe is happening, the evidence behind it, which customers it affects, what I would fix first, what I would leave alone for now, and how long I think meaningful change will realistically take.
Retention Readiness Diagnostic
Working forward from customer value
01
Get clear on the job the customer hired you to do
What was this customer actually trying to accomplish when they bought from you? What problem were they solving, or what progress were they trying to make?
And just as importantly: does Sales understand that? Does the team responsible for delivering the experience understand it? Does that context survive the handoff?
The question isn't “Do you have an onboarding process?” It's “What are we trying to make this customer successful at?”
02
Define what value actually looks like
The job tells us what the customer hired you to accomplish. Now we define what success actually looks like.
What outcome would make them say this worked? What evidence demonstrates it? Who needs to experience the value, and who needs to see it?
Those aren't always the same person.
A user can be getting tremendous value while the person making the renewal decision has no idea. That's a retention risk even when the customer looks healthy.
03
Pressure-test the path to value
Once we're clear on the job and what success looks like, we work through the experience that's supposed to get the customer there: the Sales-to-post-sale handoff, onboarding, activation, time-to-value, ownership, milestones, delivery against what was sold, and the cross-functional dependencies in between.
The question isn't whether each of those things exists. It's whether they reliably get the customers you're selling today to meaningful value.
A model that worked for yesterday's customer may not work for the customers you're selling today.
04
Make sure you'll know when something changes
Retention isn't static. Champions leave. Priorities shift. The customer's business changes. The job they hired you to do can evolve or disappear altogether.
So the last question is: will you know when the conditions for retention change?
We identify the signals that would tell you something important has changed, whether those signals are visible today, who owns them, and whether someone would notice early enough to act.
Will you know when the conditions for retention change — early enough to do something about it?
Different starting points. Same question underneath.
What has to be true for a good-fit customer to get meaningful value from what you sell — and keep choosing you?
If they're already leaving, we work backward to find where that broke.
If they're not, we work forward to make sure the conditions are there before the retention number tells you they weren't.
The shared diagnostic discipline
Get the whole story, find the pattern, test it against the evidence.
Both engagements rely on the same discipline: talk to the people who see different parts of the story, look for the patterns across what we hear, and use the evidence you already have to test what holds up. Then I tell you what I think is actually happening — and what matters most.
01
Deep conversations
The people inside your company already know a lot about what's working — and what's not. The problem is that no one person sees the whole picture. Your executives have one view. Your managers have another. The people talking to customers every day know things that never make it into an executive meeting. And your customers have their own version of the story. My job is to put the whole picture together.
I'm not your boss. I'm not the CEO. I don't sit in the org chart and I'm not defending a process I designed three years ago — so people tell me things they don't tell each other.
- Establishing trust quickly
- Asking the question behind the question
- Hearing the inconsistencies between accounts
- Following an unexpected thread wherever it goes
02
Evidence
We use the information and data you already have to test what the conversations surface: whether a pattern holds, how widespread it seems to be, which customers it affects, and whether the evidence supports what we're hearing.
03
Pattern recognition
I've spent 15+ years seeing different versions of these problems — across early-stage companies and enterprises, consulting and operating roles, software, hardware, and human-delivered services. Those repetitions matter. I know the failure modes, I know where to look, and I can recognize when something that looks like one problem is actually another.
Pattern recognition tells me where to look. The evidence tells us whether the pattern is actually yours.
04
Diagnosis + priorities
The point isn't to hand you everything I found. It's to tell you what matters. I separate symptoms from causes, identify the few issues creating the most risk, and tell you what I would address first — and what I wouldn't spend time fixing right now.
Then I give you a practical, sequenced plan your team can actually execute.
My job is to figure out what matters, tell you the truth, and give you a practical plan to execute.
Diagnose before prescribing
Most retention work starts with the solution already chosen: a new health score, a new QBR cadence, a new segmentation model, a bigger Customer Success team, an onboarding redesign, another dashboard.
Any of those might turn out to be the right answer. But until we understand why your good customers are leaving — or where the conditions for future churn are being created — we'd just be guessing.
The diagnosis comes from the evidence, not from a predetermined answer.
What you get
A well-informed answer on what matters — and what to do next.
This is a bounded engagement: roughly four to six weeks, interview-heavy, supported by the data you already have, and built to end in a clear diagnosis and a prioritized plan rather than an open-ended workstream.
You end up with a diagnosis you can trust and a plan your team can actually run.
And then it's yours
After years of doing this work, I hold a strong view that executing on it belongs with the full-time members of your team. I'm not angling for follow-on execution work — which I think makes the diagnosis better. It isn't shaped by what I'd be good at delivering next. It's shaped by what's actually true.
The primary deliverable is a concise executive diagnostic. It answers:
- The question we came in trying to answer
- The few issues actually driving the problem or creating the most risk
- The evidence behind each finding
- Which customers and segments are affected, and how
- What to do about it, and what to do first
- What not to spend time on right now
- A practical sequence your team can run
- How long the change should realistically take
- Where relevant, a clearer way to tell the retention story to your board
Why an outsider
I've spent 15+ years solving customer retention and growth problems from almost every angle.
Leadership roles and management consulting, early-stage through enterprise, including LinkedIn, Hewlett Packard Enterprise and Workrise. For nearly two years I've been doing this independently with early-stage technology and tech-enabled businesses.
The point of that breadth isn't the résumé. It's repetitions: I've seen different versions of the same value-delivery and retention problems in a lot of different environments.
I'm good at getting into a company quickly, talking to a lot of different humans, figuring out what they're really trying to tell me, and recognizing patterns. I know enough to know what to look for, but I don't come in assuming I already know the answer.
That's a useful combination for diagnostic work. It's also why this work is often better done by an outsider.
I'm not the boss. I'm not the CEO. I'm not defending the process I designed three years ago. People can tell me things they may not tell each other, and I can follow the thread wherever it goes.
Angles I've worked from
- Early-stage companies and huge ones
- Management consulting and operating roles
- Technology and tech-enabled services
- Software, hardware, and human service operations
Industries
- Education
- Insurance
- Automotive
- Energy
- Oil & gas
- Internet technology
- Computer hardware
Operator experience, consulting discipline, pattern recognition, an ability to get people talking, and no agenda about what the answer needs to be.
My job is to figure out what matters, tell you the truth, and give your team a practical plan to execute.
Get in touch
If retention is moving the wrong way, or you want to find the churn you're creating before it shows up in your numbers, send me a note. Tell me what you're seeing and we'll figure out whether this work is a fit.