Two moments are forcing companies to answer questions they don't have real answers to yet: a liquidity event that puts your growth and retention story in the spotlight, and a board asking where the AI budget affected revenue. Same underlying problem, hope standing in for evidence, different timing. I run the same revenue-first method against both, working from your actual numbers, not a hopeful narrative.
Different timing, same underlying question: is there real, measurable evidence behind what you're telling investors, your board, or yourself.
A genuine diagnostic of whether your retention and service model can actually defend against the AI-commoditization argument, followed by the investor-facing story built from what's real, not what's hoped.
Fewer than 2% of CEOs can say exactly where AI is being used in their own company, let alone what it's returning. This names every initiative, classifies it, and assigns a real owner before another dollar goes toward a tool nobody's measuring.
Some conversations work better as a short note rather than a scheduled call. If that's you, send me a quick email with your situation, your numbers, even just a question, and I'll reply personally.
kevin@yamanostrategies.com →Here's the bad news first. Nobody gets a pass on this anymore, not because your retention looks fine on paper, not because your customers love you. Investors have learned to ask the AI-vulnerability question of everyone, and a healthy business that can't answer it clearly still takes a discount it didn't earn. Now the good news: for most companies, the real numbers already make the case. They just haven't been pulled out, proven, and told as a story an investor can act on.
Thin AI-wrapper products, sold cheap to curiosity-driven buyers with no switching cost and no service layer underneath the tool, are running closer to 23% gross revenue retention. That number is real, and it's what's driving investors to ask the question of every seller in the room, including the ones it was never really about.
Traditional B2B SaaS, real service, real switching cost, real accountability structure, holds up far better: median net revenue retention around 106%, enterprise monthly churn under half a percent. If that's closer to your business, the defense already exists inside your own numbers. Building it into a story investors believe is the actual work.
This is a tried and true method, run the same way every time, whether the client is a nine-figure SaaS company or a family business deciding whether to expand. It's not a framework I sell. It's the sequence I've used to find every real gap I've ever found, tested across industries for nineteen years.
Not where you believe it flows. The P&L, or the closest real equivalent, comes before the website, the ad account, or the org chart.
Higher multiple, a clean exit, provable retention, whatever it is, named plainly, not assumed.
Most of the time it doesn't. It points somewhere the team stopped noticing a while ago.
Specifically. This is usually the moment a leadership team says nobody had ever told them that directly.
A diagnosis without a next step is just an expensive opinion. I don't leave you with one.
Most leadership teams treat churn, competitive loss, and unmeasured gaps as one undifferentiated problem, and prescribe one undifferentiated fix. Ordered from what typically costs the most to what typically costs the least, here's what the audit actually finds. Only one of these buckets is addressable through the service and ownership changes most advisors reach for first.
Usually the largest bucket. Includes the build-versus-buy and AI in-housing losses investors are specifically worried about. This is a narrative and differentiation problem, not a service problem, and it's the one this diagnosis is built to answer.
"No reason recorded." Often the second-largest bucket, and the most urgent to fix first, because no other bucket's diagnosis can be trusted while this one stays large.
M&A, acquisition, genuine business closure on the customer's side. Real, and it has to be netted out before any recovery target is honest.
Adoption, onboarding, time-to-value, account ownership structure. The genuinely addressable slice, and usually the smallest of the four, notably smaller than leadership hopes.
I've operated at the intersection of marketing, sales, product, and finance for two decades, most recently as Head of Marketing at TapClicks, reporting directly to the CEO with no marketing leadership above the role. Before that, I served as Head of Investor Relations for a public company during its NASDAQ uplisting process, presenting the growth and financial story directly to institutional investors, a rare combination for an operator to bring into a retention or exit conversation.
What sits underneath the resume is broader still: three decades working inside real estate, enterprise hardware and networking, commercial bandwidth, digital media, ad operations, and data, on top of the SaaS and consumer brands above. That range isn't a distraction from the diagnostic method, it's why it works. A revenue problem rarely respects departmental lines, and most advisors only ever learned to look at one of them.
Twenty minutes is usually enough to know whether there's a real gap worth closing before you're in front of investors, or whether your story already holds up better than you think.
See Where You Stand →