In Depth

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.

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.

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.

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.

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.

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.

Jeanne DeWitt Grosser, Vercel's COO who scaled GTM teams at Stripe, talks about building systems that let decisions happen without you. She covers balancing strategic vision with hands-on execution. She describes hiring loops and workshops that reveal thinking. She explains driver trees, metric definitions, and designing org forums to align teams.

Anil Varanasi, Co-founder and CEO of Meter, offers a fascinating look at building a sustainable networking infrastructure company. He shares his unconventional approach of thinking in 25-year horizons and discusses the lessons learned from scrapping a year of R&D due to open-source alternatives. Anil highlights the importance of business model innovation, emphasizes avoiding excessive planning methods like OKRs, and reveals how surviving challenges like Apple's M1 transition shaped their strategy. His passion for thoughtful, long-term growth inspires founders to consider their company's endurance.

Join Jyoti Bansal, co-founder and CEO of Harness and the brain behind AppDynamics, as he shares insights from his journey in scaling enterprise software. He discusses how to overcome mid-market growth barriers and why he intentionally let go of Netflix as a customer. Jyoti explains the concept of 'product-market-sales fit' and how to build a capacity-driven go-to-market strategy. He also reveals his unique approach of running 16 'startups within a startup' to foster innovation while maintaining accountability.

Zack Kanter, Founder and CEO of Stedi, shares his journey from turning $2,500 into a successful auto-parts business to revolutionizing the healthcare industry with an API-first approach. He discusses the challenges of bootstrapping, the eight iterations of his EDI product before finding product-market fit, and the concept of 'eating glass' to emphasize hard work and commitment. Zack also explores the impact of operational excellence and why his company embraces a culture of high accountability and resourcefulness.