June 04, 2026

Greg Ceccarelli — Cut Twice, Measure Once

1 hour 4 minutes

Greg Ceccarelli is Chief Product Officer at Spec Story, an AI-first startup building tools to make AI coding easier and safer. Before Spec Story, Greg held product leadership roles at Pluralsight (CPO), GitHub, Dropbox, and Google, and earlier spent years as a consultant at Alixpartners and IBM.

In this conversation, Greg and Tom cover:

Moving fast vs. planning — Greg's "cut twice, measure once" philosophy, why most decisions are reversible, and what happened when he pushed back on a private equity firm's annual planning process

AI and software development — How AI agents are compressing implementation time, changing the economics of software, and flipping the traditional "longest pole in the tent" from engineering to decision-making

Spec Story and Stoa — How Spec Story started by preserving AI chat history for developers, and why Stoa is now focused on capturing collaborative meeting context so teams can move from decision to implementation faster

SaaS pricing — Why seat-based pricing is past its expiration date, and how Stoa's $5/hour model is designed to remove friction, align with value delivered, and eliminate the token-opacity problem

The future of SaaS — Headless software, API-first systems, and whether agents will make traditional UI obsolete

Distribution and marketing — Why distribution has gotten harder, not easier, why authentic human content outperforms engineered content, and what questions every founder needs to keep asking about their customer

Core competency — Greg's answer: asking questions, and the compounding value of learning velocity over specialization

...more