In this episode, I sat down with Ryan Johnson, CPO at CallRail, a $100M+ PLG company serving over 200,000 businesses. Ryan’s path into product wasn’t traditional - he started in finance and operations before scaling product orgs at companies like Virtue (acquired by Oracle), Banjo (SoftBank-backed), and now CallRail.

We spoke about how he leads with transparency and trust, and what it takes to scale product in a high-growth, AI-driven company.

In this episode:

• How CallRail launched its Voice AI assistant from POC to product in months

• Navigating trade-offs in AI onboarding, PLG vs sales motion, and time-to-value

• What exec-level decision-making actually looks like from a CPO seat

• The difference between fundraising stories and reality -from $100M rounds to Oracle acquisitions

• How to find your “PM stage fit” and build a career with self-awareness

If you’re a PM navigating scale, new tech, or just figuring out what kind of product leader you want to become - this will be an fun and interesting listen!