Schematic is building the infrastructure layer between the application and the billing system — solving the entitlements problem that quietly kills commercial agility at scaling software companies. In a recent episode of BUILDERS, we sat down with Fynn Glover, Co-Founder & CEO of Schematic, to learn how a lived operator problem and 100 discovery conversations led to a conviction that entitlements management is to monetization what Auth0 was to authentication.

Topics Discussed:

• The entitlements problem: why hard-coding feature access to billing plan IDs creates commercial and technical debt

• How 100 discovery conversations surfaced product engineering as the true ICP — and why finance and sales couldn't see it

• The two-sided market thesis: legacy companies forced to re-architect and startups who can avoid the mess

• Why content was Schematic's primary GTM mechanism before the product existed

• How Fynn mines transcripts for language shifts and re-runs WTP validation every six months

GTM Lessons For B2B Founders:

• Use your own experience as the discovery opener: Fynn didn't lead with structured questions. He shared his story — six months to change pricing at a high-growth cybersecurity company — then listened for prospects to name the root cause before he did. When they stopped blaming the billing system and started describing the app-to-billing intersection as the problem, he had signal. Finance and sales couldn't see it. Product and engineering could, because they were building the glue.

• Separate "is this a problem" from "would you buy a solution": Once Fynn had consistency on the problem, he ran a distinct step — asking whether the infrastructure felt core to the company's product or non-core, careful not to bias the answer. The more he heard "none of this is related to our actual product," the more conviction he built that companies would buy it off the shelf. Two questions, sequenced: the first surfaces pain, the second surfaces build/buy intent.

• Publish before you have a product when creating a category: Fynn knew Schematic would take years to build something enterprises would trust. Content became the mechanism to attract people who believed in the problem before a product existed. His framing: content doesn't need direct ROI — it needs to bring the company energy, reputation, and market utility.

• Re-run willingness-to-pay every six months: Fynn ran 10-15 WTP conversations before founding Schematic and has continued every six months with new prospects and existing customers. Pricing assumptions drift — recalibration keeps positioning grounded in what buyers actually value now.

• Treat call transcripts as a language intelligence feed: One of the biggest workflow changes for Fynn has been mining call transcripts to track how buyers describe their bottlenecks over time. As the market shifts from seat-based to hybrid pricing, buyer language shifts too. Transcripts let him track that at scale rather than relying on intuition.

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