In Depth

The fastest way to learn is to run two competing bets | Jay Parikh (EVP CoreAI, Microsoft)

What startups get wrong about enterprise | Lindsey Scrase (COO, Checkr)

How Gamma pulled off their AI pivot | Jon Noronha (Co-founder and CPO of Gamma)

Why Plaid’s COO cold-calls new hires | Eric Sager (COO of Plaid)

Leading a company through periods of intense volatility requires a relentless focus on long-term value creation for customers and the ecosystem, rather than fixating on singular milestones like acquisitions or funding rounds. Success hinges on building a resilient culture that prioritizes customer needs and empowers te...

How Supabase became the essential infrastructure for the AI era | Paul Copplestone (Co-founder, CEO)

How to build a beloved tech brand | Sheila Joglekar Vashee (CMO, Figma)

Why old-school sales work still wins in the AI era | Graham Moreno (Head of GTM, Parallel)

Why founders should bet on first-time executives | Praveer Melwani (CFO, Figma)

Figma CFO Praveer Melwani details his professional evolution from an individual contributor to a public company executive, emphasizing the necessity of first-principles thinking and deep operational involvement. Success in the finance function requires moving beyond mere compliance to act as a strategic partner who und...

Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)

The role of an excellent Chief Product Officer centers on setting strategic vision, understanding customers deeply, and managing resource allocation rather than overseeing every feature. Success requires adapting to the specific dynamics of the CEO—whether a visionary founder or an operational executive—and maintaining...

Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)

Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)

Operating "atoms-oriented" businesses, such as DoorDash, requires a rigorous focus on unit economics and operational details that differ significantly from "bits-oriented" software companies. Executives must maintain the ability to dive into granular data—like investigating delivery failures at the store level—to ident...

The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)

Chief People Officer Katie Burke details the strategic evolution of the people function, emphasizing that internal communications and culture must ladder up to business objectives rather than serving as a "nanny state." Effective people leadership requires building a high-performance environment where managers act as c...

What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)

The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)

The discussion centers on the role of a Chief Product Officer (CPO) in a scale-up startup, drawing on Jeremy Epling's experiences at Microsoft, GitHub, and Vanta. Epling emphasizes the need for CPOs to be deeply involved in product details, advocating for a "founder mode" approach. He highlights the importance of maint...

Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)

Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)

Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)

Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)

The discussion centers on defining the role and success metrics of a design function within a software company. Ryan Lucas, design leader at Rippling, argues that design, like engineering, is fundamentally about problem-solving, drawing from humanities, social sciences, and arts. He emphasizes that design's job is to c...

Executive Function: Building systems that can make decisions without you | Jeanne DeWitt Grosser (COO, Vercel)

The discussion centers on the qualities that distinguish exceptional executives in scaling startups, featuring Jeanne DeWitt Grosser, COO of Vercel. A key attribute is the ability to operate effectively at both a strategic (30,000 feet) and operational level, simultaneously developing long-term visions and addressing i...

Building Meter for decades, not an exit | Anil Varanasi (Co-founder and CEO)

In this episode of the podcast, Brett Berson interviews Anil Varanasi, the co-founder and CEO of Meter, a networking infrastructure company. Anil discusses Meter's long-term vision of owning the entire technology stack, including hardware, software, and operations, to build a generational company. He emphasizes the imp...