Sam Gardner recently joined the go-to-market team at Anthropic after his previous company, Stainless, was acquired by Anthropic.

Sam is not a software engineer, but he is one of the most technical non-engineers I’ve talked to. He represents a new kind of operator who sits between sales, product, engineering, and automation, and uses code and AI to stitch all of it together.

In this episode, we talk about what go-to-market actually looks like at a company like Anthropic, how Sam uses AI in his day-to-day work, how he broke into companies like Ramp, Salesforce, Stainless, and Anthropic, and where AI is useful versus where it becomes a crutch.

If you’re interested in software engineering, AI, startups, or the future of work, I think you’ll get a lot out of this conversation.

This is a conversation with Jeff Escalante, who’s currently a Director of Engineering at Clerk, where he spends more than 80% of his time writing code.

Before that, Jeff was an early engineer at HashiCorp, where he joined around 200 employees and stayed through the company growing to thousands of employees and eventually IPOing. During that time, he also became a prominent contributor to Next.js, which led him to join Vercel as the manager of the Next.js team, where he helped shape the roadmap for one of the most important frameworks in web development.

In this episode, we talk about how Jeff broke into software engineering without a traditional CS background, how to get hired without spraying your résumé everywhere, what he’s learned from spending most of his career in dev tools, how Clerk thinks about engineering, and how AI is changing the way software engineering actually works.

Hope you enjoy the first episode, and welcome to the podcast.