Most early-stage healthtech teams are ready on the thing they built. The gap is almost never the model, the pipeline, or the interface. It is the operational layer around it: how a plan buys it, what it costs them to run it, and whether anyone can prove it was worth it twelve months later.
Everything here happens before a dollar moves, and most of it happens in rooms you are not in.
Not "improves outcomes." PMPM, admits per thousand, readmission rate, MLR points, Star or HEDIS measure movement, avoided spend against a named baseline.
A plan cannot fund a line item that does not map to a number someone already owns.
Free pilots and co-creation are not free. If implementation needs twenty hours a week from a clinical ops leader or a data engineer, that is the real price, and it is the thing that quietly kills deals. Name the roles and the hours.
The economic buyer, the operational sponsor, and every function that can stop it: security, privacy, legal, compliance, procurement.
Then the honest calendar, including security review, BAA, and where you land relative to their budget cycle.
"We are on GCP and it is HIPAA compliant" is not an answer to a plan security questionnaire. SOC 2 status, penetration test results, subprocessor list, data retention and destruction, breach notification terms, where PHI physically lives.
Breakeven is not the bar. This cost sits on their side of the line, which makes it the hardest thing for you to see and the easiest thing for you to underestimate. Every hour their staff spends running, monitoring, correcting, or working around your product is subtracted from the return you promised in the buy case. If you cannot estimate their operating cost, you do not actually know what your ROI number is.
Not a sample file. Not a spec you wrote. Large national plans are not modifying their feeds for you. You take what they send, in their format, on their schedule, with their quirks.
And everyone designs for the happy path. The question is what your system does when the file arrives late, arrives twice, arrives with a column silently renamed, or does not arrive at all. Who finds out, how fast, and what happens to your output in the meantime.
Claims lag. Retroactive adjustments that change last quarter's numbers. Member versus patient identity across enrollment, claims, and clinical systems. Multiple member IDs for one human. Mid-year plan changes.
These look like edge cases until they are most of your data.
Measured against the workflow they have, not the one you wish they had. Improving the workflow is the goal. Not making it worse is the requirement.
A tool that adds a screen to a nurse's day loses regardless of how good the model is.
Someone has to verify you are doing what you said. Who reviews your output, how often, against what.
If the answer is that their team spot-checks your results indefinitely, you have handed them a job, not a solution.
The renewal is decided long before the renewal conversation, and usually by someone defending the spend without you in the room.
Not the data you would request. If your proof requires a feed they never agreed to send, you will be arguing from anecdote at the moment it matters most.
Monthly updates, quarterly reviews, a standing format. Plans experience vendor silence as risk.
The cadence is not overhead. It is the mechanism by which anyone inside the plan can defend the spend.
Not how many seats are licensed. Whether their people and yours are actually solving problems together: has their operational knowledge changed your roadmap, have you changed how they think about the problem, is there a standing working relationship below the executive level.
Products that are merely used get cut in a budget cycle. Products built with a customer have someone inside the plan who argues for them.
Single-threaded accounts do not renew. Name your champion, name the second relationship, and name what you would do the week you find out they took another job.
Opens your own mail client with the scores filled in. Nothing leaves your browser until you press send.
If one of these questions landed uncomfortably, that is usually the useful part. The uncomfortable ones tend to be the reason a deal is sitting still.
I do fractional product and data work with early-stage healthtech, mostly on exactly this layer. Happy to talk through whatever scored a zero, whether or not it goes anywhere.
Shawn@AtypicalStrategicInsights.com
Shawn Leffler
Atypical Strategic Insights
Fourteen years payer-side at Horizon and Anthem across claims, care management, behavioral health, and analytics. Currently fractional Chief Product Officer for a Medicaid engagement platform.