In Depth

Guest Matt MacInnis, COO at Rippling and former CEO at Inkling, shares insights on culture, org-design, and product strategies. Topics include characteristics of great CEOs, leading with kindness and impatience, and fighting entropy in business. The discussion delves into hands-on leadership, effective marketing strategies, and the importance of first principles thinkers in go-to-market teams. Additionally, the episode explores anti-patterns in business success, organizational behavior, and the journey of self-acceptance and empowerment.

Former CEO of Square, Alyssa Henry, shares insights on navigating different tech cultures, lessons from Amazon, Microsoft, and Square, and the importance of 'Minimum Remarkable Products'. Discussion includes insider reactions to AWS launch, exploring pioneer vs. fast-follower companies, and balancing priorities in tech giants.

Guest Adam Nash discusses building platforms, delighting customers, disrupting donor-advised-funds, LinkedIn strategy lessons, leadership transitions. Insights on successful digital platforms, strategic decision-making, interconnectedness of product and company strategy, product development at LinkedIn, Wealthfront and Robinhood strategies, intentional product design for customer delight.

Eilon Reshef, Co-founder at Gong, shares insights on recording sales calls, finding product-market fit, design partnerships, AI in B2B sales, and the future of AI. The episode covers lessons from riding the AI wave since 2015, expanding into multi-product offerings, and the importance of design partners in scaling a startup.

Learn from Dennis Pilarinos, founder of Unblocked, as he shares culture/product lessons from Amazon, Apple, Microsoft. Dive into building/scaling DevTools, finding product market fit, dealing with AI complexities, and prioritizing mental health as a founder. Discover common hiring mistakes and key insights on team dynamics and product success in the tech industry.

May Habib, CEO of Writer, delves into scaling AI products for enterprise, importance of champions, healthy co-founder relationships, and the future of agentic AI. Discusses advice for AI founders in 2024. Highlights investing in smaller AI models for specific use cases and building a business with strong team dynamics.

Amjad Masad, co-founder and CEO of Replit, discusses how AI is reshaping the software landscape, bridging the gap between ideas and software, Replit's fundraising difficulties, the secret lever they pulled to scale ahead of competition, and Replit's impressive distribution engine.

Michael Cieri, CPO at Gusto and former Head of Product at Square, shares key product strategies, building for SMBs, pros and cons of vertical SaaS, moving faster in product teams, developing intuition, and impactful individuals at Square.

Stephanie Berner, Customer Success Executive at LinkedIn, discusses common customer success mistakes, building a world-class customer success org, tactics for hiring exceptional talent, and where customer success fits into the wider org. She shares successful strategies from Box, Medallia, and LinkedIn. Topics also include early-stage customer success metrics, addressing churn problems, building trust with customers, connecting customer success with product development, and determining the size of a customer success team.

Michael Lopp, experienced engineering leader at Apple, Palantir, and Slack, talks about his 'utopia' where engineers have time to create, what makes an excellent engineering leader, navigating internal dynamics between design, engineering, and product, and key lessons from over 30 years in the industry.