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Episodes


Inside Guideline's mission to modernize 401(k)s | Kevin Busque (Co-founder and CEO)

Inside Braze’s blitz to $500M in CARR | Building broad, going global, and outfoxing the competition

Clay's unconventional path to $1.25B: Rethinking GTM, pricing, and enterprise sales | Varun Anand

Building a $4B data platform: Inside dbt Labs' unconventional path | Tristan Handy (Founder & CEO)
Tristan Handy, CEO of dbt Labs, details the company’s evolution from a data consultancy into a $4.2 billion venture-backed enterprise. Initially built as an internal productivity tool to solve data transformation challenges, dbt gained traction through an open-source model that fostered a self-sustaining user community...

How Figma taps into taste, simplicity, and storytelling | Yuhki Yamashita (CPO)

How to find customers in the Dept of Defense: From prototype to the Pentagon | Steve Blank

Shifting Career Altitudes: Insights from a CPO That's Led Nearly Every Function | Anneka Gupta

How to find & pull startup growth levers | Matt Lerner (Founder of SYSTM, Author of Growth Levers)

How to find — and keep — product-market fit | Bob Moore (Crossbeam, RJMetrics, Stitch Data)

Rebooting Intercom: Eoghan McCabe on Defying Silicon Valley Orthodoxy | Co-founder & CEO
In this episode of the In-Depth podcast, Brett Berson interviews Eoghan McCabe, co-founder and CEO of Intercom, about his experience leaving and then returning to the company to reshape its direction. Eoghan reflects on trusting his intuition, moving away from Silicon Valley best practices, and focusing on customer nee...

Inside marketing at Stripe, OpenAI and Retool | Krithika Muthukumar (VP of Marketing at OpenAI)

Developing technical taste: A guide for next-gen engineers | Sam Schillace (Microsoft, Google Docs)

How to build and scale winning marketplaces | Casey Winters (Eventbrite, Pinterest, Grubhub)
Successful marketplace scaling hinges on owning demand and establishing proprietary, scalable acquisition loops rather than relying on unsustainable paid marketing. Liquidity—the rate at which supply and demand interact—serves as the critical indicator of product-market fit, often requiring founders to perform non-scal...

Lessons from Sentry on scaling DevTools and finding product market fit (again) | Milin Desai (CEO)

How to be effective up and down the org chart | Matt MacInnis (Rippling, Inkling, Apple)

Timeless lessons from Square, Amazon and Microsoft | Alyssa Henry

Ironclad's Path to Product-Market Fit

Lattice's Path to Product-Market Fit

Verkada's Path to Product-Market Fit
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