5 Sales Mistakes That Kill Health Tech Deals (And How to Fix Them)

Let’s be honest: Selling into healthcare is a minefield.

You can have a great product, strong early interest, even a signed pilot… and still end up ghosted, stalled, or shut down by "other priorities."

Over the years, I’ve worked with dozens of health tech companies — from pre-revenue startups to $20M+ scale-ups — and I’ve seen the same avoidable sales mistakes sabotage deals again and again.

These aren’t generic SaaS problems.

They’re healthcare-specific execution gaps — the kind that kill momentum, waste your team’s time, and leave real revenue on the table.

Here are five of the biggest mistakes I see, and how to fix them before they blow up your deal.

1. Selling the Vision, Not the Problem

Founders love to pitch the big idea:
“We’re transforming care.”
“We’ll reduce readmissions by 20%.”
“We personalize medicine at scale.”

Great. But your buyer? They’re underwater in a staffing crisis, have six tools they’re not using properly, and twelve dashboards they never look at.

The Fix:
Lead with a current, painful, specific problem — not your product vision. Solve a today-problem that aligns with something they’re already focused on (staffing, patient throughput, compliance, documentation, etc.). Then back into the bigger picture later.

Pro Tip: Anchor your message to external pressure they already care about — like CMS mandates, NCQA ratings, HEDIS measures, or internal quality initiatives.

2. Running Pilots With No Expansion Plan

A health system offers to run a pilot. You say yes. You celebrate.

But there’s no exec sponsor. No defined outcome. No timeline. No conversation about what happens if/when the pilot works.

Six months later, the pilot ends. And you’re no closer to a real deal.

The Fix:
Treat the pilot like a formal engagement. Define success metrics up front. Identify who needs to approve a full rollout. Get buy-in on what happens when it works. If you can’t get answers to those questions, you should seriously evaluate IF you should do the pilot.

Pro Tip: Include a “Pilot Success Criteria” slide in every kickoff deck. Make adoption part of the plan — not an afterthought.

3. Only Engaging the Clinical Champion (Ask Me How I Know)

Years ago, I was working with a medium-sized, innovative hospital. We had a care management solution, and the clinical team loved it. We got a pilot going quickly and saw great early results.

But I made a rookie mistake: I focused entirely on the clinical champion. I didn’t engage senior leadership. I didn’t build alignment outside of the pilot team. I assumed the early success would speak for itself.

It didn’t.
 

The project died. Leadership deprioritized it. Too many other things going on. End of story.

The Fix:
Map all the stakeholders early. Talk to finance. Talk to IT. Talk to operations. Talk to whoever controls budget and strategic priorities. Don’t let one champion carry the entire load.

Pro Tip: Ask your champion, “Who else needs to be involved to make this successful?” Then go meet them — now, not later.

4. No Reimbursement or Funding Strategy

Healthcare orgs don’t just want ROI. They want to know how they’ll actually pay for your solution.

Even if you deliver measurable outcomes, the question is:
 Where does the budget come from?
Is it reimbursed? Operational? Grant-funded? Included in value-based contracts?

If you don’t have an answer, the deal dies.

The Fix:
Clarify the economic model early. Know whether your solution is covered under CMS, tied to a payer incentive, or needs to be budgeted as a tech line item. Make this part of your sales narrative — not something procurement has to figure out on their own.

Pro Tip: Add a “How It’s Funded” section to your sales deck or proposal. You’ll look more prepared — and you’ll speed up internal buy-in.

5. Underestimating the Chaos

Healthcare is full of smart people… buried in competing priorities, political landmines, and bureaucratic gridlock.

Even when your buyer says yes, the wheels turn slowly.

Someone retires. The EHR migration derails your project. A system-wide initiative pulls funding.

None of this has anything to do with you — but it still affects your deal.

The Fix:
Don’t expect linear sales cycles. Build momentum intentionally. End every call with a defined, meaningful next step. Follow up with value. Keep moving the process forward — or it will drift by default.

Pro Tip: Create a simple “Decision Map” to visualize every step between pilot and full adoption. Share it. Adjust it. Make blockers visible early.

Wrapping Up

A lot of health tech products fail — not because they don’t work, but because they’re sold like generic SaaS.

You need more than a good demo.

You need to understand the ecosystem.

You need to navigate internal complexity, clarify reimbursement, and close the gap between pilot and adoption.

That’s what I help health tech teams do every day.

Want to fix a stuck pilot, uplevel your sales team, or just get one deal over the finish line?

Let’s set up a quick call →

I’ll help you figure out where your deals are stalling — and what to do about it.