How We Rebuilt Our Pricing Around Real Company Growth

If you’re like most of the founders I work with, you’ve had this thought more than once: “The way we’re doing this part of the business isn’t wrong, but it’s not quite right either.”

Maybe it’s your pricing model. Maybe it’s your organizational structure. Maybe it’s your strategy. But something in your gut keeps tugging at you. You feel misaligned — not with your market, necessarily, but with where you are now and what you know a great company should look like.

That’s where I was about a year ago.

I knew our per-user pricing wasn’t working well for early-stage teams or companies trying to bring all their team members into the platform. It just didn’t feel right. But changing it meant touching nearly every part of the business, from product and engineering to finance, data, marketing, and customer support. It also meant stepping into the unknown during a period when the overall economy is a bit of a mess. Nothing about the timing was ideal, but it was work that had to be done (and a decision we didn't take lightly). 

This is the story of what happened when I finally said, “Let’s fix it.” Disclaimer: It took longer than I thought. It got messier than I expected. And even now, I still don’t know how it will play out.

But I know we made the right move. And if you’re facing a similarly difficult decision, I hope this helps to give you some clarity.

When the Model Stops Serving the Customer

At Ninety, we’d been using a per-user pricing model for years. It was clean, scalable, and predictable. But we started hearing the same feedback over and over again:

“I want to get my whole team on Ninety, but I can’t justify the cost yet.”

“I don’t need all these features yet — I just need the basics so I can grow.”

These were symptoms of friction, misalignment, and a model that no longer matched our vision.

We help teams focus, align, and thrive. That starts with inclusion. And a model that disincentivizes bringing your whole team on board? That just wasn’t us.

So, we began working on something bigger: a commercial model that aligned not just with where companies are but with where they’re going.

Why It Took So Long, And Why It Was Worth It

Like many belief-driven decisions, this one was messy. Over the course of a year, we talked with hundreds of users — founders, integrators, team leaders, BOS coaches. We ran dozens of financial models. We worked with pricing experts from Strata and Pricing I/O to help us challenge our assumptions. And the complexity wasn’t just theoretical.

• Engineering had to rebuild foundational components of the platform.
• Data and finance ran model after model, weighing trade-offs between simplicity, scalability, and fairness.
• Product and marketing redefined how we position value across multiple customer profiles.
• Customer success helped us design for edge cases and communicate with clarity.

Every choice became a balance — a balance of flexibility vs. simplicity, perceived value vs. actual engagement, and optimizing for stage vs. creating future lock-in.

It wasn’t easy. But if you’re working to build a great company, you already know: Easy is rarely the right filter. It’s humbling to realize how much coordination, trust, and teamwork it takes to pull off a change like this. And it reminded me why I love building companies in the first place.
It also reminded me that great companies aren’t built by founders alone. They’re built by teams who rally around something they believe in. That’s what happened here.

Aligning with the Stages of Development

Eventually, we realized we weren't just redesigning pricing. We were designing for the Stages of Development.

In the early stages of building a business, companies need simplicity and access. In the later stages, they need insight, visibility, and enterprise-grade capability. One size wasn’t just inefficient — it was a friction point.

So we built a tiered structure:

• Free for founders who need to get out of spreadsheets and into structure.
• Essentials for teams ready to run solid Weekly Team Meetings, set Rocks, and build accountability.
• Accelerate for Stage 3–4 companies needing quarterly planning, performance tracking, and insights to scale intentionally.
• Thrive for those playing the long game, ready for enterprise readiness, AI capabilities, and full systemization.

And we launched our All-In Offer, a 30% discount when you bring your whole company into Ninety. Because momentum happens when everyone’s aligned.

Trust Is the Real Strategy

It’s tempting to view pricing changes as strategic levers. But at its core, this was a trust decision.

Trust in our clients, believing they’d respond to alignment over discounts.

Trust in our team, that we could deliver this shift without breaking stride.

Trust in our vision, that doing what’s right, even when it’s uncertain, will lead to better outcomes.

That trust isn’t abstract. It’s rooted in Ninety’s worldview and in the three dimensions of trust we teach: character, competency, and connection.

Our new tiered commercial model is more aligned with how companies grow. And it reflects our belief that when companies bring everyone in — when they go all in — they thrive.

So this wasn’t just a pricing strategy. It was a trust decision. I trust that if we give more away, more companies will trust us. And over time, that will lead to more value for everyone — our customers, our coaching partners, and us.

Designing for the Age of Understanding

I deeply believe we’re in the middle of a massive shift in how Work works. I call it Work 8.0: the Age of Understanding.

In this new age, people don’t just want a paycheck. They want purpose. They want to matter. They want to work inside organizations that trust them — and that they can trust in return.

Our platform changes reflect that evolution. Here's what’s new:

• Maz: Our AI-powered work companion, which is now in beta, helps you draft Rocks, prepare for meetings, and resolve issues.
• Insights Reporting: Surface performance trends, track health, and make decisions backed by real data.
• Mobile App: Lead from wherever you are with the same clarity and accountability.
• Knowledge Portal: Document once, scale forever. Build process consistency at every level.
• Integrations: This allows you to connect with Microsoft, Google, and more on the way.

These aren’t bells and whistles. They’re tools for helping founders build companies that thrive in a high-trust, high-purpose world.

So, Will It Work?

If you’re expecting a tidy bow here, I hate to disappoint you, but I don’t know exactly what this shift will do to our revenue in the short term. We've modeled it (more than we probably should have). But models are just that: models.

What I do know is this: We made this decision from a place of deep alignment. We acted in accordance with our Core Values and Focus Filters. We built a structure that evolves with companies, not past them.

And that’s what great companies do. They design for evolution, not just efficiency.

What You Can Take From This

If you’re in the thick of a decision (whether it’s about your pricing, product, or processes), here are five questions I’d ask you as a fellow founder:

1. Where do you sense your customers are feeling friction?
2. What would it look like to align your model with how your Ideal Customers actually grow?
3. What decision would you make if you trusted your beliefs more than your forecast?
4. Are you building a system that works today or one that grows with your company?
5. Does the team around you have the Competency, Commitment, and Capacity to execute a change this big, or do you need to invest before you leap?

Answering these questions won’t give you certainty, but it will point you toward clarity. And in a founder’s world, clarity is the compass you need when certainty isn’t available.

Let’s Keep Building

At Ninety, we’ve rolled out the new plans. We’ve launched the All-In Offer. And we’re seeing early signs of strong adoption: The Ninety mobile app reached #46 in Apple’s Top 100 Business Apps within a day of launch, and it just keeps getting better.

If you’re already a Ninety client, thank you, thank you, thank you!!! This shift is for you.

If you’re new to us, now’s the best time to start because things just got a whole lot better.

If you’re a founder trying to decide whether to bet on your beliefs, I hope this gives you some perspective. Because sometimes doing what you think is right means living with uncertainty for a while.

That’s part of the Work.

Want to explore Ninety’s updated plans? Compare plans or go all in.