Pricing AI Is Hard: 8 Lessons (and a Few Scars) from 12 Years at Salesforce

Pricing AI is hard in a way SaaS pricing never was: the costs are real, they move week to week, and the old playbook of seats and platform tiers wasn't built for it. Glenn Dearing spent 12 years running pricing at Salesforce and later led it at UKG. He's joining Turnstile’s CEO, Jordan Zamir, to talk through what that taught him and how much of it survives the shift to AI.

Glenn is bringing eight hard-won lessons, each with the story and the scars behind it.

A few you'll hear:

• Predictable beats perfect. A pricing metric customers can't forecast is worthless — no matter how well it tracks value.
• Fungible credits. How to pass falling model costs on to customers without triggering a painful repricing event.
• Ship before you're right. We shipped a token model we knew wouldn't last, because a quarter of real feedback beats a quarter of being right on paper.
• Legibility over transparency. Publishing your price isn't enough until customers can explain your model back to you.

He'll test every lesson against the AI era — what still works, what GenAI just broke, and what revenue and finance leaders should be building now. Jordan joins to dig into the infrastructure that has to keep up: the metering, quoting, and billing underneath pricing that changes.

Glenn Dearing — Managing Partner, Vantage Line
Glenn has spent more than two decades monetizing innovation. He spent 12 years in pricing at Salesforce, most recently as SVP of Pricing Strategy, where he priced everything from the core platform to Force.com, Heroku, and Shield. He went on to lead global pricing and strategy as GVP at UKG, and earlier ran pricing at NXP and advised high-tech and consumer companies at McKinsey. Today he co-runs Vantage Line, a monetization consultancy helping software companies price through the AI era.

Jordan Zamir — CEO & Co-Founder, Turnstile
Jordan Zamir is CEO & Co-Founder at Turnstile, an AI-first quote-to-cash platform for modern SaaS companies. He previously served as General Counsel and CFO at high-growth startups including Second Measure (acquired by Bloomberg) and Minted. His experience in those roles exposed him to the operational friction that broken quote-to-cash processes create in scaling companies. He built Turnstile to solve that problem—delivering a quote-to-cash system designed for operators who prioritize speed and flexibility without administrative burden.