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From Bump to a Billion Users: My Hard‑Won Product Lessons from David Lieb and Google Photos
Read more: From Bump to a Billion Users: My Hard‑Won Product Lessons from David Lieb and Google PhotosI unpack lessons from David Lieb’s journey building Google Photos, from early Bump missteps to scaling past one billion users. The core themes are precise product discovery, problem-led prioritization, and crisp user interviews that validate needs—not solutions. I highlight how to stack rank canonical users, align roadmaps to outcomes, and avoid spreading across edge cases.…
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Build Scalable Startup Systems: My Take on Kevin Fishner’s Writing-First, KPI-Driven Playbook
Read more: Build Scalable Startup Systems: My Take on Kevin Fishner’s Writing-First, KPI-Driven PlaybookI break down how Kevin Fishner, Chief of Staff at HashiCorp, scales company-wide systems as the organization grows to over 1000 people. You’ll see exactly how meetings, goal tracking, and decision-making through writing create a repeatable operating cadence. We’ll dive into annual planning with a business simulation, a scorecard system, and weekly and quarterly rhythms…
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Treat Operational Debt Like Tech Debt: Inside Elastic’s Distributed Work Playbook
Read more: Treat Operational Debt Like Tech Debt: Inside Elastic’s Distributed Work PlaybookI share my takeaways from a deep dive with Leah Sutton, SVP of Global HR at Elastic, on how a “distributed by design” organization scales with clarity and speed. We unpack hiring for remote leadership, the realities of payroll and compensation across regions, and practical moves to reduce language and cultural barriers. I also outline…
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Twilio’s CEO on Peaks, Valleys, and C-Suite Truths: Hard-Won Lessons for Product Leaders
Read more: Twilio’s CEO on Peaks, Valleys, and C-Suite Truths: Hard-Won Lessons for Product LeadersJeff Lawson’s journey at Twilio is a masterclass in product leadership under real-world constraints. I break down the rationale behind launching a second product early — and the safeguards that keep focus intact. I also unpack the Uber wake-up call and how to mitigate customer concentration risk before it becomes existential. You’ll see why I…
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Unleash Employee Engagement: Proven OKR fixes and manager playbooks for startups
Read more: Unleash Employee Engagement: Proven OKR fixes and manager playbooks for startupsI break down battle-tested strategies to boost employee engagement and manager effectiveness. You’ll learn how to apply the “direction-coaching-career” framework, avoid common OKR pitfalls, and focus on outcomes vs output. I share tactical prompts for feedback, questions to uncover what your team really thinks, and overlooked items for employee engagement surveys. I also highlight 13…
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Inside Tido Carriero’s Playbook: Build World-Class Engineering Orgs and Nail Product/Market Fit
Read more: Inside Tido Carriero’s Playbook: Build World-Class Engineering Orgs and Nail Product/Market FitI reflect on Tido Carriero’s path from Facebook to Dropbox to Segment and the leadership systems he uses to build high-performing engineering orgs. You’ll learn how to apply single threaded leadership responsibly and use the black box analogy to assess team performance. I also share practical guidance for the IC to manager transition and how…
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Build a People-First Org: Data-Driven Empathy, Skip-Levels, and Career Growth with Mark Frein
Read more: Build a People-First Org: Data-Driven Empathy, Skip-Levels, and Career Growth with Mark FreinI share lessons from a conversation with Mark Frein, the Chief People Officer & Head of Alumni Programs at Lambda School, on building a people-first organization powered by data and empathy. You’ll learn how to align the employee experience with your company’s competitive positioning, just as you would a product strategy. I break down practical…
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Inside Product-Led Growth: Self-Serve, Pricing, and Prioritization Lessons from Kate Taylor
Read more: Inside Product-Led Growth: Self-Serve, Pricing, and Prioritization Lessons from Kate TaylorI sat down with Kate Taylor to unpack the playbook behind product-led growth and effective self-serve motions. We discussed how to move upmarket without sacrificing efficiency, and how to structure product prioritization — including Notion’s system of 700 tags and real tradeoffs. We also dove into pricing and packaging, from Dropbox experiments to why Notion’s…
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From Instacart to Anomalo: Elliot Shmukler’s Zero-to-One Playbook for Product Leaders
Read more: From Instacart to Anomalo: Elliot Shmukler’s Zero-to-One Playbook for Product LeadersI break down Elliot Shmukler’s shift from Instacart growth leader to founder/CEO of Anomalo and the zero-to-one lessons that matter most. You’ll learn how he prioritizes time, avoids tire-kicker prospects, and applies poker-inspired decision-making. I share how to adapt those practices for founder-led GTM, product discovery, and product-market fit. We also cover CEO communication habits…
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From Zero Customers to IPO: Eric Berg’s Hard-Won Playbook for the Messy Middle
Read more: From Zero Customers to IPO: Eric Berg’s Hard-Won Playbook for the Messy MiddleEric Berg’s career offers a precise roadmap from 0 customers to IPO, with actionable lessons across ICP definition, early go-to-market, and zero to one B2B marketing. I unpack the “messy middle,” including moving upmarket and building a pricing and packaging model that can unlock new heights. I also highlight cultural patterns like hiring for the…
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Ask Why It Won’t Work: Hard-Won 0→1 Lessons, Pre-Mortems, and Founder-Led GTM from Persona
Read more: Ask Why It Won’t Work: Hard-Won 0→1 Lessons, Pre-Mortems, and Founder-Led GTM from PersonaI sat down with Rick Song of Persona to unpack a disciplined 0 to 1 approach that pairs pre-mortems with founder-led GTM. Persona recently announced a $50 million Series B, plans to double the team, and revenue that’s surged more than 10x — with customers including Square, Postmates, and Gusto. Rick’s focus on asking why…
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From Slack’s ‘Where Work Happens’ to CEO: Inside the Product Strategy That Scales
Read more: From Slack’s ‘Where Work Happens’ to CEO: Inside the Product Strategy That ScalesI explore how Kelly Watkins, CEO of Abstract, moved from a marketing background to the CEO seat and why that matters for product strategy. Her alternative to yearly planning, borrowing from famed strategist John Boyd, aligns with agile roadmapping and faster feedback loops. I highlight how optimizing for trade-offs, not absolute right or wrong, strengthens…
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