Lenny's Podcast: Product | Career | Growth

Jessica Fain, a product leader at Webflow and former Slack chief of staff, gets into why great ideas fail without buy-in. She explores how executives make decisions, why the first minute of a meeting matters, and how to disagree without becoming political. They also dig into presenting options, aligning with company strategy, and why AI makes influence even more valuable.

Jacob Warwick, an executive negotiation coach and former founder, shares a sharper way to ask for more without sounding pushy. They get into why negotiation starts long before the offer, how to dodge the comp expectations trap, why interviews should feel like discovery calls, and the subtle language that can unlock surprisingly big moves.

Michelle Rial, illustrator and author known for viral chart-based books, discusses her new children’s book Charts for Babies and her creative process. She talks about how simple, emotional visuals spread and where her chart ideas come from. They also explore creativity routines, iteration, and turning everyday insights into teachable moments.

Qasar Younis, co-founder and CEO of Applied Intuition and former Y Combinator COO, built software that adds autonomy to vehicles and heavy machines. He discusses why AI’s biggest wins will come in farming, mining, construction and trucking. He explains different autonomy approaches, why he stayed under the radar while building the company, and the values that drive his team.

Jenny Wen, head of design for Claude at Anthropic and former Figma design director, discusses why the classic discovery→mock→iterate process is fading. She contrasts execution/support work with visionary direction. She shares a day-in-the-life at Anthropic, her AI toolstack, why Figma still matters for exploration, and what she looks for when hiring designers.

Jeetu Patel, President and Chief Product Officer at Cisco who leads massive AI and product efforts, discusses Cisco’s AI-first transformation and organizing 30,000 people around AI. He covers Cisco’s role in AI infrastructure, constraints like compute and trust, his six-part framework for building companies, communication strategies to prevent message loss, and how he thinks about leadership and strategy at scale.

Boris Cherny, Head of Claude Code at Anthropic and creator of Claude Code, led the rapid rise of agentic AI for developers. He recounts Claude Code’s origin, surprising design lessons like starting in the terminal, and why coding feels solved. They explore agents expanding beyond code, Cowork’s quick build, experimentation culture, and how teams should structure work and safety around AI tools.

Brian Halligan, co-founder of HubSpot and Sequoia’s in-house CEO coach, shares scaling battle-tested advice. He explains his LOCKS framework, why hiring “spiky” candidates beats consensus picks, and how to build teams like the 2004 Red Sox. He also explores why starting a company is easier today while scaling is harder, and why enterprise sales may be the last white-collar role AI replaces.

Sherwin Wu, Head of Engineering for OpenAI’s API and developer platform, leads work on the API, Agents SDK, and developer tools. He discusses how Codex rewrites software workflows. Short takes on AI cutting review times, engineers managing fleets of agents, widening productivity gaps, and why now is a rare window to leap ahead before roles fully transform.

Lazar Jovanovic, a professional vibe coder who builds production AI products without a traditional coding background. He explains why non-technical perspective helps, why planning and chat time beat raw prompting, and how parallel prototypes, persistent PRD/Markdown context, and a 4x4 debugging workflow keep AI-built apps reliable. He also argues design judgment will become the most valuable skill in the AI era.