EVOLVING ON PURPOSE

You know the feeling if you’ve been running a company for a while. Nothing’s broken, exactly, but it’s not quite right anymore either. You keep pushing forward, but the friction builds until you realize the system you’ve been relying on no longer aligns with who you’ve become.

That was the case with our pricing model at Ninety. It had served us well. But then we started hearing from customers — leaders who wanted to bring their whole team into the platform but couldn’t justify the cost. Early-stage teams didn’t need every feature. What they needed was access, inclusion, and clarity.

So we made a call. Not to tweak the model, but to rebuild it. We listened, tested, debated, and weighed trade-offs across every team in the company. What emerged was a pricing structure that better reflects how companies actually grow.

Read more in How We Rebuilt Our Pricing Around Real Company Growth.

This wasn’t just about pricing. It was about alignment and trust. And it reminded me that the hardest changes usually come when things are almost working.

The hard truth is this: Building a great company means choosing to evolve, even when it would be easier not to.

PERSPECTIVES

“Growth begins at the end of your comfort zone.” — Neale Donald Walsch

MARK MY WORDS

This decision touched nearly every part of the business — Product, Engineering, Finance, Marketing, Customer Success. It took longer than I thought. It got messier than I expected. And I still don’t know exactly how it will play out.

But I’m confident we made the right move.

We didn’t overhaul pricing because it was broken. We did it because it no longer aligned with where we are, who we serve, and what we believe about growth. That kind of change is never clean. It’s uncomfortable. It forces you to trust your people, principles, and process.

Great companies evolve on purpose. And sometimes the hardest decisions are the ones where nothing is clearly wrong, but something isn’t quite right.

TUNE IN

Recession-Proof Leadership: Building an Antifragile Company

When a recession hits, some companies break. Others adapt and grow stronger.

In this Founder’s Framework podcast episode, I explore how to lead through uncertainty and build a company that can weather any storm.

You’ll learn:

• How to assess if your company is built for tough times
• Why antifragility is more powerful than resilience
• How Forever Agreements help teams stay aligned under pressure

[Watch Now]

ONE MORE FOR THE ROAD

In case you missed it, here’s more from Founder’s Framework:

In My Opinion: A Polymathic Perspective

The best founders don’t rely on one lens. They draw from history, psychology, business, and beyond to solve real problems with real context. In this article, I share why the Work 9.0 mindset means evolving across disciplines and leading with both clarity and curiosity.

[Read Now]