Author:
Look, I can predict this one from across a trade show floor now.
A founder tells me the pilot went great. Clinicians used it. The metrics held. The medical director called it the best thing he'd seen in years. Then eleven months go by — no contract, no expansion, no renewal. Just a polite email about budget shifting to next fiscal year.
Here's the thing. The pilot was never the sale. It was the audition for the sale. And most companies walk offstage thinking they got the part.
I've spent 25 years selling into risk-averse institutions — Fortune 50 floors at IBM and Kodak, then the startup side, and before that, copiers. Copiers teach you what no playbook does: the best product in the room loses all the time. What wins is knowing how the decision gets made.
So here's a quick flyover of where these deals die.
You sold to the champion. Nobody else.
Your champion is real. She loves it. She'll say so on a reference call. And she cannot buy anything.
Behind her is a committee, and every seat has a different fear. Your technical evaluator fears a breach or a broken integration. Compliance fears a finding. Finance fears a number that won't hold up. The end user — the nurse, the coder, the scheduler — fears you're about to make her day longer. Procurement fears a bad contract. And the executive who signs fears one thing only: looking like he backed the wrong horse in front of a board.
Most founders respond by sending the champion a deck and hoping she carries it. Seriously, don't do that. You're asking the one person with no authority to defend you in a room you've never entered, against objections you've never heard.
Give her something she can forward without editing. A business case sized for finance. Security answers written for the CISO, not for her. That's not a nice-to-have. It's the whole game.
You treated security and compliance as paperwork at the end.
I watch companies run a beautiful clinical pilot for six months, get a verbal yes, and then get handed a 300-question security questionnaire. That adds four months minimum. Sometimes it kills the deal outright, because you can't answer forty of the questions and now the CISO has an opinion about you.
In healthcare, security and compliance are not the last gate. They're the long pole. Put them at the front — HIPAA, data handling, architecture, penetration results — while the clinical conversation is still warm. It feels premature. Do it anyway.
Right? Better to fail a control in month one than month nine.
You called on people who were never going to write a check.
This is the one I see most from founders entering US healthcare from outside, and it's the most expensive.
They assume there's a buyer. Singular. They call a few hospitals, land a pilot, and figure the checks follow. But this market has thousands of payers, self-insured employers, systems, and health plans that all buy differently, budget differently, and answer to different regulators. A pilot at one hospital tells you almost nothing about the one down the road.
I had a client burn $4 million going door-to-door to doctors. Four million dollars, one practice at a time, in a market where the margin was sitting in self-insured employer groups the whole time. Seriously, don't do that.
So before you spend any time with a prospect, answer three questions. Does this person have the problem you solve, badly enough that they say it out loud? Can they write the check without begging a committee two floors up? And is something forcing them to move in the next twelve to eighteen months — a contract expiring, a mandate, a metric somebody's bonus depends on?
Miss any one of the three and you don't have a prospect. You have a very expensive conversation.
You hired a rep to fix a problem a rep can't fix.
Here's the pattern. Growth stalls, the founder is exhausted, so the company hires a salesperson. Eighteen months and a couple hundred thousand dollars later, that person is gone and everyone concludes it was a bad hire.
It usually wasn't. You handed someone a job with no defined buyer, no qualification criteria, no process to run, and no way to inspect whether it was working. Nobody closes into that. You didn't hire the wrong person — you hired before there was anything for them to run.
Seriously, don't do that either. Build the thing first, then hire someone to operate it.
The uncomfortable part
You can brute-force your way to a million dollars. Plenty of founders have, on sheer will and a good product and a lot of nights nobody saw. Past that, will stops scaling and the math turns on you.
The companies that break through aren't the ones with better technology. They're the ones who figured out that revenue is a system — a defined buyer, a repeatable way to reach every seat at the table, a process a team can run and a manager can inspect — and built it before they needed it.
So if you're coming to Las Vegas in November with a pilot that worked and a pipeline that never followed, that gap isn't a product problem. It's an architecture problem, and architecture is fixable.
Come find me on the floor and tell me where yours stalled — which seat at the table went quiet, what month the deal stopped moving. I'll tell you what I've watched kill it before. I'd rather you learn this from my scars than go buy your own.
Dan's book, 'Seriously, Don’t Do That: A Founders Field Guide to Building a Revenue Engine that Scales Without You', will be released in early November
