In Depth
First Round
Welcome to In Depth, a podcast from The First Round Review that’s dedicated to surfacing the tactical advice founders and startup leaders need to grow their teams, their companies and themselves. Hosted by Brett Berson, a partner at First Round, In Depth will cover a lot of ground and a wide range of topics, from hiring executives and becoming a better manager, to the importance of storytelling inside of your organization. But every interview will hit the level of tactical depth where the very best advice is found. We hope you’ll join us. Subscribe to “In Depth” now and learn more at firstround.com
Episodes
Mentioned books
44 snips
Apr 30, 2026 • 50min
Why great product leaders should stop obsessing over the roadmap | Diya Jolly (CPO & CTO of Xero)
Diya Jolly, Chief Product and Technology Officer at Xero who previously led product at Okta and Google. She discusses why leaders should raise team ambition, the need for protected startup-like innovation within big orgs, taking bigger roadmap risks in the AI era, delegating decisions with a three-bucket framework, and protecting weekly thinking time to make high-impact choices.
12 snips
Apr 21, 2026 • 57min
Inside Artemis' "AI vs AI" war | Shachar Hirshberg & Dan Shiebler (Co-founders, Artemis)
Shachar Hirshberg, a veteran security leader from AWS and Palo Alto, and Dan Shiebler, an ML engineer with Twitter and Abnormal pedigree, discuss building an AI-native security company fast. They cover hiring for AI fluency, founder-market fit, early customer obsession, engineering AI-first detection, and how AI accelerates both attacks and defenses.
60 snips
Apr 17, 2026 • 1h 2min
Scaling DoorDash to market dominance | Christopher Payne (Former COO, DoorDash)
Christopher Payne, former President and COO of DoorDash and ex-Amazon/eBay ops leader, shares scaling playbooks. He contrasts atoms vs software, explains his plate-spinning framework for executive attention, and details protecting new product S-curves. He also covers hiring builders, why leaders must keep technical detail, and the case for top-down ambitious goals.
50 snips
Apr 10, 2026 • 1h 11min
The most politically dangerous role in the C-suite | Katie Burke (COO, Harvey)
Katie Burke, former HubSpot people leader turned COO at Harvey, known for building culture and people strategy. She talks about treating HR like marketing, why hospitality hires shape culture, the long cultural hangover after layoffs, clear rules for feedback, and how AI will reshape people operations and managers’ time.
29 snips
Mar 26, 2026 • 1h 7min
What nobody tells engineers about becoming a CEO | Jay Kreps (Co-founder and CEO, Confluent)
Jay Kreps, co-founder and CEO of Confluent who built Apache Kafka at LinkedIn, reflects on moving from engineer to CEO and the new skillset that requires. He recounts Kafka’s rocky open-source launch and the long blog post that sparked adoption. He also explains why Confluent doubled down on a cloud-first path and the strategic choices that made that survival bet.
148 snips
Mar 19, 2026 • 1h 10min
The product wisdom every CPO should ignore | Jeremy Epling (CPO, Vanta)
Jeremy Epling, Chief Product Officer at Vanta and former product leader at Microsoft and GitHub, reflects on moving from big tech to startup life. He discusses staying close to product details, keeping shipping velocity as teams scale, owning final decisions at the C‑level, and running open office hours to demystify leadership.
23 snips
Mar 12, 2026 • 1h 11min
Building Zipline: From launch disaster to drone-delivery giant | Keller Cliffton (Co-founder, CEO)
Keller Cliffton, co-founder and CEO of Zipline (drone delivery pioneer that started with medical flights in Rwanda), shares the origin story from a failed home-robot startup to lifesaving drone logistics. He talks hiring unconventional talent, rapid scrappy hardware testing, brutal but fast personnel decisions, and how a bold Rwanda pitch and chaotic launch led to massive scale.
169 snips
Feb 26, 2026 • 60min
Snowflake’s first sales hire on scaling from $0 to $3.5B | Chris Degnan (Former CRO, Snowflake)
Chris Degnan, Snowflake’s first sales hire and long-time CRO who scaled revenue to billions, shares war stories and playbook moves. He unpacks how the CRO role changes with scale. He emphasizes MEDDIC as a must-know methodology. He explains how to spot fakers, build scalable GTM motions, and what relentless leadership and hiring discipline really look like.
114 snips
Feb 19, 2026 • 1h 11min
Why 90% of CROs will fall behind in the next 2 years | Stevie Case (CRO, Vanta)
Stevie Case, CRO of Vanta and former pro gamer turned sales leader, shares a nontraditional path into revenue leadership. She discusses why early revenue hires fail. She explains what top CROs actually do. She reflects on a scaling mistake at Vanta and why the company stays sales-led. She debates AI versus humans in go-to-market and planning 24–36 months ahead.
91 snips
Feb 12, 2026 • 1h 6min
Figma is not the source of truth | Ryan Lucas (VP of Design, Rippling)
Ryan Lucas, VP of Design at Rippling and trained industrial designer with founding experience, shares big-picture design leadership lessons. He talks about design’s role in product success. He outlines the four pillars of design management. He explains staying hands-on, escaping perfectionism, scaling judgment, and why the customer-facing product—not Figma—is the source of truth.
