E203: From Sentry to Modem - Rethinking How Product Teams Listen

In this episode, our co-hosts Robby and Tim talk with Modem Co-Founder Ben Vinegar who's building the AI product manager for software teams. He was previously a longtime engineering leader at open source application monitoring software platform Sentry. Ben reflects on his journey from Disqus to nearly a decade at Sentry, where he became the company’s first VP of Engineering and worked across product development, SDKs, acquisitions, and incubation. He shares how the rapidly falling cost of software development with AI led him to build Modem, an AI product teammate that helps teams understand what customers are saying and connect that feedback to what they’re shipping.The conversation explores why data and context, not just the agent, are the hard parts of building useful AI products, how conversational data creates a new kind of observability, and why these systems are harder to build internally than they appear. He also discusses open source, dogfooding, and how being deeply fluent with AI is changing the way he hires and builds teams.