How I Learned to Win Founder Negotiations Using Pricing and Leverage

Welcome back to Founder Mode!

Happy Thanksgiving!

Before we begin, I would like to express my gratitude.

Thanks for reading.

Thanks for building.

And thanks for being part of this journey.

Let’s get into it!

How Founders Win Negotiations: Pricing, Leverage, and Value

Most founders spend a ton of time building the product and almost no time thinking about how to price it. That used to be me, too.

With Pretty Good AI, we’ve had to figure this out quickly. We’re in healthcare. That means high expectations, lots of gatekeepers, and long sales cycles. So we’ve learned how to position, price, and negotiate in a way that works for both sides.

This isn’t just about “closing deals.” It’s about gaining momentum with the right customers. We need to keep our team focused and create deals that drive growth.

Here’s what’s working for us.

1. Pricing Isn’t Just a Number. It’s a Strategy.

We used to think pricing was about picking a flat rate. Now we think about how to align price with value.

Here’s what we focus on:

• A clear monthly platform fee
• A usage-based model charges per call or interaction. It gets cheaper as volume increases.
• Setup fees? We usually waive them
• Annual contracts? Not yet—we stay flexible

Like I said in our recent Founder Mode episode:

That mindset has made all the difference.

2. Use Time as a Lever: Contract Lengths

Typical SaaS playbooks push multi-year contracts with steep discounts. We’re doing the opposite.

At Pretty Good AI, we keep it simple:
​Month to month. No lock-in. No fine print.

We believe that if the product delivers real value, customers will stay. If it doesn’t, they should leave.

This forces us to build a better product—every single month.

As I’ve said before, we want to earn the right to serve our customers, not trap them with terms.

3. Win Deals by Delivering First

We don’t rely on past projects or half-built demos. We prove value right away, with real insights.

When a new practice starts with Pretty Good AI, we don’t jump straight to selling. First, we deliver a detailed set of analytics and optimization opportunities for free.

It’s how we show them we understand their workflows, their pain points, and what better could look like.

It’s not just a sales tactic. It’s how we build trust early.

As I’ve said before:

4. Every Customer Gets Custom—Without Custom Pain

We’re not selling hours or building for the sake of it. What we offer is outcomes.

Today, thanks to AI, every customer gets a product that feels like it was built just for them, because in many ways, it is.

Custom used to be expensive and rigid. But we’ve built Pretty Good AI to be flexible by design. That means we can tailor the experience to your practice without starting from scratch.

The value is in what it does for you, not how long it took us to build it.

As I like to say:

5 Key Takeaways

1. Flat fees are simple to understand. Tying prices to usage and results builds stronger relationships.
2. Monthly Beats Multi-Year Skip the long-term contracts. Month-to-month pushes us to do better and builds customer trust.
3. Lead with Real Insight. Instead of pitching, we show practices on how we can help. Analytics first, demo second.
4. Make Custom Feel Easy. With Pretty Good AI, every solution feels like it’s made just for you. Also, there's no expensive price or tricky software needed.
5. Own the Outcome. Our goal is to earn the business, not win the deal. That means focusing on results from day one.

Final Thoughts

Most founders don’t talk about pricing until the last minute. I used to be that way, too.

But what I’ve learned—especially building in healthcare—is that how you price, how you position, and how you negotiate are part of the product.

When you show up with confidence, clarity, and a plan that works for both sides, people feel it.

You don’t need to over-explain. You just need to deliver.

Thanks again for being part of this community.

Enjoy the holiday. Rest, recharge, and keep building.

See you tomorrow,

-kevin

Recent Social Posts

Kevin Henrikson @KevinHenrikson Selling software month to month is freeing. Even the sales leaders I talked don’t want to do it. They are afraid customers will churn. True founder mode ensures alignment with your customers every day to re-earn their business. If your product is great why need lock in? 4:25 AM • Nov 20, 2025 0 Retweets 2 Likes

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Kevin Henrikson @kevindegods You can hack your way to traction. You cannot hack your way to scale. The shift from founder hustle to system design separates the survivors from the headlines. 6:1 PM • Nov 19, 2025 5 Retweets 22 Likes Read 10 replies

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