Pricing is a strategic decision wearing a number's clothing. Get it right and it carries the business; get it wrong and it quietly caps everything you build on top of it.

On a recent episode of the SaaS Stories podcast, I had the pleasure of speaking with Fynn Glover, founder of Schematic, about his route from startup founder to pricing specialist — including the mistake that cost him most, and how founders can build a pricing strategy that survives scale.

Listen to the full episode of SaaS Stories with Fynn Glover

From soccer to SaaS

Fynn's path wasn't conventional. Growing up in Tennessee, his ambitions ran toward professional soccer. Two jobs after college, one at a startup and one at a hedge fund, redirected him into business and technology instead.

In 2012 he launched his first company as a location-based app for outdoor enthusiasts, which became a media business, and eventually a SaaS company selling content marketing software to e-commerce and direct-to-consumer brands. That pivot into software is where his interest in pricing and product strategy began.

He scaled the company to 30 employees and exited through an acquisition, then joined a cybersecurity company at Series C — an education in later-stage problems and in how much pricing shapes growth. In 2023 he founded Schematic with a team of experienced colleagues, built around helping SaaS companies get their pricing architecture right from the beginning.

The mistake that mattered

Ask Fynn about the biggest error of his first company and he doesn't hesitate: he misunderstood the market's willingness to pay.

This wasn't a rounding problem. It was a fundamental gap between what the product was worth in customers' eyes and what the company was charging, and it constrained growth in ways that were difficult to see from inside.

His answer is early and structured willingness-to-pay conversations. Done properly, they show you what the market thinks your product is worth, strip out founder bias, place you against adjacent tools and competitors, and let you set price on feedback rather than assumption.

How to run a willingness-to-pay exercise

Fynn uses an eight-question framework with prospects and customers. Two questions carry most of the weight.

Relative value perception. "How valuable is this product compared to other software tools you're currently paying for?" This locates you in the customer's stack, which is the single best indicator of the price band you can occupy.

Maximum willingness to pay. Open-ended: "Now that you've seen the product, what's the maximum you'd pay per month or per year?" Or anchored: "If this were priced at $X per month, how would that affect your intent to buy?"

The point isn't a number. It's finding out whether your pricing and your adoption goals are compatible.

Pricing is a process, not a decision

The most common mistake in SaaS is not updating pricing often enough. It should evolve alongside your product and your market, which means a few habits worth building.

Run the exercise every six to twelve months. Make increases incremental — an annual adjustment of four or five percent is far easier for customers to absorb than a sudden jump. And tie pricing to the roadmap, so new features show up in what you charge rather than accumulating for free.

Feature flagging as a pricing tool

Feature flagging started as a DevOps practice for testing and gradual deployment. Fynn points to a growing second use: managing entitlements and pricing tiers.

It lets you test premium features with a subset of customers before a universal rollout, adjust plans by toggling features against subscription levels, and run flexible trials without back-end surgery. The result is genuine agility in packaging and upsell.

What Fynn tells founders and CTOs

Make pricing a core business function. It isn't a finance decision. It needs product, sales and engineering in the room. Set up a pricing committee that meets quarterly to review data and act on it.

Align the roadmap with the strategy. Every significant release is a chance to refine packaging and monetisation, so pricing discussion belongs inside product planning rather than after it.

Build flexibility from day one. Don't hardcode pricing logic into the application. Feature flagging and billing automation are what make later changes possible without an engineering project.

A lesson from experience

Asked what he'd tell his younger self, Fynn talked about apprenticeship. Starting a company young taught him resilience, but working under an experienced entrepreneur first would have accelerated his learning on scaling, pricing and sales considerably.

His advice to aspiring founders is refreshingly unglamorous: work for a startup before you start your own. You'll pick up the critical lessons without paying full price for each one.

If you're going to act on one thing here, run the willingness-to-pay conversation with ten customers this month. It's free, and it's the fastest way to find out whether your pricing reflects your market or just your own assumptions.