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Moments That Changed Us: Teresa Torres & Petra Wille on Leadership, Loyalty, and Product Discovery
Read more: Moments That Changed Us: Teresa Torres & Petra Wille on Leadership, Loyalty, and Product DiscoveryThis candid conversation with Teresa Torres and Petra Wille explores the moments that permanently shape how we lead and build products. You’ll hear why prioritization is survival—not a backlog exercise—and how “No one knows the answer” can unlock agency in uncertain times. The episode surfaces hard-won lessons on loyalty, burnout, and the importance of boundaries,…
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Why I’m Tuning In to “In Depth”: Tactical Playbooks for Startup Hiring, Leadership, and Growth
Read more: Why I’m Tuning In to “In Depth”: Tactical Playbooks for Startup Hiring, Leadership, and GrowthThis preview instantly signaled a rare focus on actionable, operator-grade advice. The show spans executive hiring, manager development, and organizational storytelling—topics that matter when you’re scaling product and people. I’m listening for frameworks I can apply immediately, from outcomes vs output OKRs to product roadmapping and sprint planning. Expect deep dives that support the IC…
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What I Learned from Molly Graham: Hard-Won Management Lessons from Google, Facebook & Quip
Read more: What I Learned from Molly Graham: Hard-Won Management Lessons from Google, Facebook & QuipI share hard-won management lessons from a conversation with Molly Graham, who helped scale Facebook, Quip, The Chan Zuckerberg Initiative, and Lambda School. Learn why many startup mistakes trace back to general management issues and how to avoid the common traps. I explain why you should spend more time with your highest — not your…
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Going ‘Unreasonably Deep’: Hard-Won Product Lessons with Ayo Omojola from Cash App to Carbon Health
Read more: Going ‘Unreasonably Deep’: Hard-Won Product Lessons with Ayo Omojola from Cash App to Carbon HealthI sat down with Ayo Omojola to unpack how to build products in regulated industries and why going “unreasonably deep” creates an edge. We dive into problem selection, showing how choosing the right problem compounds across discovery, roadmapping, and execution. Ayo shares frameworks for process, setting context, and “optimizing for the outstanding,” which I’ve seen…
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Hard-Won CEO Lessons: Steve El‑Hage on Pivots, Burnout, and Rebuilding After a Revenue Cliff
Read more: Hard-Won CEO Lessons: Steve El‑Hage on Pivots, Burnout, and Rebuilding After a Revenue CliffSteve El‑Hage’s hard-won journey spotlights the realities of first-time leadership: revenue cliffs, painful pivots, hiring missteps, and burnout. I unpack how founder-led GTM and rigorous product discovery turn setbacks into product-market fit lessons. You’ll see why outcomes vs output OKRs anchor pivots, and how better hiring loops improve employee retention at startups. I also share…
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Start With the Story: Leadership Lessons from Drift’s David Cancel I Use to Elevate Teams
Read more: Start With the Story: Leadership Lessons from Drift’s David Cancel I Use to Elevate TeamsI build product organizations around one principle: start with the story. David Cancel’s approach at Drift shows why storytelling isn’t fluff—it’s a core operating system for product, marketing, and sales. In this piece, I share how I apply his lessons, from screenplay-inspired onboarding to executive communication that zooms in and out with precision. I break…
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Win-Win Partnerships: Stripe & Notion Lessons to Negotiate Smarter and Scale Faster
Read more: Win-Win Partnerships: Stripe & Notion Lessons to Negotiate Smarter and Scale FasterCristina Cordova shares hard-won lessons from Stripe and Notion that I immediately translate into product and platform tactics. You’ll learn how to frame win-win partnerships, avoid common traps as a first partnerships hire, and negotiate from strength without sacrificing long-term value. I highlight how to connect partner strategy directly to product roadmapping, activation metrics, and…
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How Atlassian Scaled Without a Sales Team: Product-Led Growth, Pricing, and Channel Plays
Read more: How Atlassian Scaled Without a Sales Team: Product-Led Growth, Pricing, and Channel PlaysI sat down with Jay Simons to unpack Atlassian’s non-consensus growth playbook — building a product that sells itself while deferring short-term wins for long-term advantage. We explored the “three-legged stool” of self-service, a global channel partner network, and enterprise upselling, and why that sequence matters. We also dove into SaaS pricing strategy and the…
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Inside Upstart’s Unlikely Rise: Dave Girouard’s playbook for pivots, speed, and hiring
Read more: Inside Upstart’s Unlikely Rise: Dave Girouard’s playbook for pivots, speed, and hiringI unpack my takeaways from a conversation with Dave Girouard, CEO and co-founder of Upstart, an AI-powered lending platform that recently went public. He shares how a business model pivot, fast execution, and flying under the radar of Silicon Valley shaped Upstart’s trajectory. I highlight why his “Are you Airbnb or Paypal?” test clarifies product…
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How Jean-Denis Grèze Builds Ownership-Driven Engineering Teams: My Leadership Playbook
Read more: How Jean-Denis Grèze Builds Ownership-Driven Engineering Teams: My Leadership PlaybookI share my takeaways from a compelling conversation with Jean-Denis Grèze, Head of Engineering at Plaid, on building an engineering culture of ownership. His journey — from law to Director of Engineering at Dropbox — underscores a philosophy of pragmatism over perfection. We explore why his engineering org doesn’t have titles, how he evaluates engineering…
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From C‑Suite to Boardroom: Anne Raimondi’s Playbook to Scale Leaders and Build Great Boards
Read more: From C‑Suite to Boardroom: Anne Raimondi’s Playbook to Scale Leaders and Build Great BoardsAnne Raimondi’s journey offers a masterclass in scaling from operator to board member. I distill our conversation into concrete tactics for C-suite readiness, including a high-signal 30, 60, 90-day executive onboarding plan. You’ll learn how to recruit and assess executives, when to promote from within, and how to avoid common hiring traps. I share my…
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The Game-Changing System Behind Kindle, AWS, and Prime—and How I Apply It Today
Read more: The Game-Changing System Behind Kindle, AWS, and Prime—and How I Apply It TodayI distill the most enduring lessons from Bill Carr and Colin Bryar’s “Working Backwards” and show how I apply them to product management leadership. You’ll see how Amazon’s “working backwards” process, Kindle/AWS/Prime origin stories, and mechanisms mindset translate into stronger product discovery and outcomes vs output OKRs. I share practical ways to make innovation a…
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