How to Win Healthcare Deals With One Smart AI Wedge


The Healthcare AI Wedge: Go Narrow to Win Big

Welcome back to Founder Mode!

I've watched dozens of AI startups try to break into healthcare. Most of them fail. Not because their technology is bad. They fail because they try to do too much at once.

Let me tell you what actually works.

Start Small, Win Big

To sell AI to hospitals and healthcare companies, I learned you need a way in.

Think of a wedge like the thin edge of a door stopper. You don't kick the door down. You slide something small into the gap. Then you push.

I saw this work perfectly with a company that focused on call centers. Just call centers. Nothing else.

Hospitals get thousands of calls every day. People are calling to schedule appointments. People are asking about bills. People are checking test results. It's chaos.

This company said, "We can fix your call center." That's it. One problem. One solution.

They didn't try to sell electronic health records. They didn't promise to revolutionize patient care. They took on the frustrating problem that kept operations managers up at night.

And it worked.

Once they got in the door through the call center, everything changed. They had access to the hospital's systems. They understood the data. They built relationships with the leadership team.

Six months later, they expanded to scheduling. Then billing. Then patient follow-ups.

The wedge worked because it was specific. It was small enough for decision-makers to say yes right away, without a long wait. It was useful enough to prove that the technology was effective.

Speak Their Language or Go Home

I can't stress this enough: healthcare people can smell a fake from a mile away.

I’ve been in meetings where tech founders talked about "machine learning" and "neural networks." The hospital executives nodded, though they didn’t seem engaged. Then, they stopped returning our calls. Why? Because the founders didn't speak healthcare.

Healthcare has its own language. It's like visiting a foreign country. You need to learn the words people actually use.

Healthcare leaders often focus on patient flow and bed usage. They worry about penalties for readmissions. They also think about how quality measures work. They also work on issues like prior authorizations and claims denials. If you talk about technology without knowing these terms, you’ll miss out. Instantly.

I learned this the hard way. I spent three months just listening. I went to healthcare conferences. I read industry publications. I talked to nurses, doctors, and administrators.

I learned that "discharge planning" is about getting patients home safely. I found that "length of stay" affects hospital revenue directly. I learned that "staffing ratios" can make or break a nursing unit's budget.

This wasn't just vocabulary practice. It was learning how healthcare actually works. What keeps people up at night. What problems cost them money. What regulations they fear.

When I finally went back to pitch meetings, everything changed. I spoke their language. I understood their world. They trusted me.

The lesson? Don't just learn healthcare terms. Learn healthcare problems. Live in their world before you try to sell them anything.

Numbers Talk Louder Than Features

Let me tell you about two different sales pitches I witnessed.

Pitch A: "Our AI platform uses smart language tools. They help improve communication and boost efficiency."

Pitch B: "We reduced call center staff from 20 people to 13 while handling more calls. The volume went from 50,000 monthly calls to 80,000. Same quality. Less cost. More capacity."

Guess which one got the contract?

Healthcare executives don't care about your technology. They care about results they can measure.

When I pitch AI solutions now, I lead with numbers. Real numbers from real customers.

"This hospital cut its average call wait time from 8 minutes to 90 seconds."

"This clinic cut scheduling errors by 73%."

"This health system saved $2.3 million in its first year."

These metrics are essential since healthcare depends on them. Every department has targets. Every leader has goals they need to hit. Every budget has items that need explaining.

When you show concrete numbers, you speak directly to their needs. You show them exactly how your solution helps them hit their targets.

I learned to connect AI benefits to healthcare outcomes. Don't just say "increased efficiency." Say "reduced length of stay by 0.8 days." Don't say "improved accuracy." Say "decreased claim denials by 15 percent."

The more specific you get, the more believable you become.

And here's a secret: small improvements matter more than you think. A hospital that cares for 50,000 patients a year might save millions with only a 5% rise in efficiency. Show them that math. Make it real.

Your Network Is Your Shortcut

Healthcare sales cycles are brutal. I've seen deals take 18 months from first contact to signed contract. Sometimes longer.

But I've also seen deals close in 60 days.

The difference? Distribution partnerships.

Let me explain what I mean. Healthcare is a relationship business. Everyone knows everyone. Organizations exist just to connect healthcare leaders.

I found success by teaming up with these connector organizations.

There are groups that buy for many hospitals. Some associations hold conferences for all decision-makers. Consulting firms work with various health systems at once.

These organizations have what you lack: trust.

When a trusted partner connects you with a hospital CEO, you’re no longer cold calling. You're not spam in their inbox. You're a trusted choice suggested by someone they admire.

I worked with a company that spent six months trying to break into a major health system. Cold emails. LinkedIn messages. Nothing worked.

We found a consulting firm that already worked with that health system. The firm will add our solution to their broader recommendations.

We had a meeting within two weeks. We closed the deal in three months.

The consulting firm got a small finder's fee. We got a major customer. The health system found a solution suggested by advisors they trusted. Everyone won.

Look for these partnership opportunities:

  • Industry associations (like the American Hospital Association)
  • Group purchasing organizations (GPOs)
  • Healthcare consulting firms
  • Technology integration partners
  • Industry conference organizers

These partnerships help you "jump the line" and get in front of real decision-makers faster.

Private Equity Needs a Guide

I picked up a new insight that shifted my strategy: private equity firms are buying healthcare companies at a quick rate.

PE-backed companies have a mandate from their investors: explore AI. Find efficiencies. Cut costs. Improve margins.

But here's the problem. These companies don't know where to start.

A PE firm buys a chain of urgent care clinics. The managing director tells the CEO, "Go figure out AI." The CEO has no idea what that means.

This is your opportunity.

These companies need to be led. They need concrete examples. They need to see what's working for companies just like them.

When I pitch to PE-backed healthcare companies, I now use case studies from their direct competitors. Not from tech companies. Not from other industries. From their peers.

"Here's what another urgent care chain did with AI scheduling. Here's what a similar radiology group achieved with AI image analysis. Here's what a competitor saved on revenue cycle management."

PE firms love competition. If their peer companies are getting ahead with AI, they feel pressure to catch up. Fast.

I found that PE-backed companies tend to move quicker than regular healthcare groups. They have clear financial targets. They have aggressive timelines. They have executive teams incentivized to show results quickly.

This means shorter sales cycles. Faster decisions. Quicker implementations.

The key is positioning yourself as the guide. Not just a vendor. Not just a technology provider. The expert who helps them navigate AI adoption step by step.

Show them the roadmap. Explain the wins their peers are achieving. Hold their hand through the process.

Five Key Takeaways

Let me break down what matters most:

1. Use the wedge strategy to get inside. Pick one specific problem you can solve really well. Get in the door with that single solution. Once you're inside and have proven yourself, expand to other areas. Don't try to sell everything at once. It's too risky for them and too complicated for you.

2. Become fluent in healthcare before you sell. Spend real time learning how healthcare works. Grasp the workflows, the language, and the important challenges. Healthcare executives can quickly see if you’re not familiar with their field. If you don't speak their language, you won't get their trust.

3. Lead with concrete numbers, not technology features. Nobody cares about your algorithms. They care about results they can measure and report to their board. Show them exactly how much time they'll save, how much money they'll make, or how many errors they'll prevent. Make the math simple and specific.

4. Find distribution partners who already have relationships. Stop cold calling. Healthcare sales take forever when you're unknown. Work with groups that already reach your target customers. Let trusted intermediaries introduce you. This cuts your sales cycle from 18 months to three months.

5. Guide PE-backed companies with peer examples. Private equity owns more healthcare companies every year. These companies have mandates to explore AI but need direction. Show them what their direct competitors are achieving. PE-backed companies move faster and have pressure to show results quickly.

Final Thoughts

Breaking into healthcare with AI is hard. But it's not impossible.

I've made every mistake possible. I've wasted months on deals that went nowhere. I focused on technology instead of results. I've tried to sell everything when I should have focused on one thing.

What I learned is this: healthcare doesn't need another technology vendor. Healthcare needs partners who know their world. They can help guide through change.

The wedge strategy works because it's low risk for your customer. Begin with small tasks to boost your confidence. Then, tackle bigger opportunities.

In healthcare, trust is key. Using the right words matters more than the tech you use.

Concrete metrics are key. Healthcare depends on data and accountability.

Distribution partnerships are important. They offer chances that cold emails can't achieve.

PE-backed companies are eager to adopt AI. They have the mandate and urgency to do so, which makes our help effective.

I'm still learning. Every customer teaches me something new. Each implementation shows what works and what doesn’t.

But if you're trying to break into healthcare with AI, start narrow. Prove your value. Earn trust. Then expand.

The wedge works. I've seen it work dozens of times. And it can work for you, too.

The opportunity in healthcare AI is massive. The need is real. The problems are urgent.

But you have to earn your way in. One wedge at a time.

See you next week,

-kevin

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Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

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