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Usage-Based, Hybrid, or Tiered? Proven Strategies to Master Your SaaS Pricing Model
Read more: Usage-Based, Hybrid, or Tiered? Proven Strategies to Master Your SaaS Pricing ModelI break down the trade-offs between usage-based pricing and traditional SaaS pricing, with practical guidance on aligning monetization to customer value. I also explore when to apply hybrid and tiered pricing, drawing on real-world lessons from Stripe’s approach. You’ll learn how to treat pricing like a product, with clear ownership, experimentation, and strong cross-functional loops.…
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Mastering International Expansion: My Product Playbook Inspired by Faire’s CEO Max Rhodes
Read more: Mastering International Expansion: My Product Playbook Inspired by Faire’s CEO Max RhodesInternational expansion can fuel breakout growth — if you time it right and execute with discipline. Drawing on insights from Max Rhodes of Faire, I break down a practical playbook for when to go global, how to staff and operate your first launches, and how to navigate local competitors. I also share how a rigorous…
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Never Done Sales? Proven GTM Playbooks I Learned from Meka Asonye at Stripe & Mixpanel
Read more: Never Done Sales? Proven GTM Playbooks I Learned from Meka Asonye at Stripe & MixpanelI break down a practical GTM conversation with Meka Asonye, highlighting founder-led sales, early pilot design, and the often-overlooked power of customer success. You’ll learn how to structure first customer calls, avoid the common leveling mistake in your first sales hire, and anchor comp to leading indicators after onboarding. We also explore choosing the right…
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IC, Manager, or Founder? Amber Feng’s Playbook for High-Impact, 0→1 Engineering Careers
Read more: IC, Manager, or Founder? Amber Feng’s Playbook for High-Impact, 0→1 Engineering CareersIn this first-person reflection, I share the most actionable lessons from Amber Feng’s journey as the co-founder and CTO of Cocoon and her eight years as an engineering leader at Stripe. I break down the traits that set high-achieving engineers apart across roles and levels. I also address the IC to manager transition with practical…
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Executive Hiring That Scales: Battle-Tested Tactics to Find the Right Leaders, Right Now
Read more: Executive Hiring That Scales: Battle-Tested Tactics to Find the Right Leaders, Right NowExecutive hiring is a leverage point that can accelerate or stall your startup. In this first-person playbook, I share why focusing on the next 18–24 months — not 5–10 years — consistently leads to better executive hires. I detail a rigorous, repeatable process for sourcing, interviewing, and reference checks, including how to test for ownership…
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Master Early-Stage Communications: Actionable Lessons from Figma, Uber, and Beyond
Read more: Master Early-Stage Communications: Actionable Lessons from Figma, Uber, and BeyondEarly-stage communications is a product strategy lever, not just a press tactic. I explore how narrative clarity reinforces founder-led GTM, product discovery, and product-market fit lessons. Drawing on insights from Nairi Hourdajian of Figma — and her experience at Uber, Canaan, and in politics — I outline how to craft foundational messaging for different audiences…
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Master Startup Compensation: Proven Tactics for Offers, Equity, and Retention at Every Stage
Read more: Master Startup Compensation: Proven Tactics for Offers, Equity, and Retention at Every StageStartup compensation is high-stakes and often misunderstood. I break down early-stage traps to avoid, a lightweight framework for broad levels and an initial comp philosophy, and practical ways to handle offer negotiation beyond base salary. You’ll learn how to explain equity (and the exercise window) to candidates new to startups, plus when and how to…
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Cracking Government Sales: Lessons on Long Cycles, Risk, and Pivoting to Product-Market Fit
Read more: Cracking Government Sales: Lessons on Long Cycles, Risk, and Pivoting to Product-Market FitSelling to government requires a different playbook: extra-long sales cycles, layers of subcontractors, and risk-averse decision-makers. I share how founder-led GTM, multi-threaded stakeholder mapping, and time-boxed pilots de-risk adoption while accelerating momentum. We also examine why the first iteration of a product may stall in the public sector and how to pivot without losing the…
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How I Build Highly Technical Enterprise Products: Hard-Won Lessons from CockroachDB and Nate Stewart
Read more: How I Build Highly Technical Enterprise Products: Hard-Won Lessons from CockroachDB and Nate StewartI distill hard-won lessons from a conversation with Nate Stewart, CPO of Cockroach Labs, the creator of database product CockroachDB. We explore how to lock onto a sharply defined use case and enforce a credible go-forward plan — even when it means saying no to misaligned customers. I share practical tactics to avoid over-commitment, treating…
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Stop Promoting Your Top ICs: “When They Win, You Win.” Lessons for Modern Managers
Read more: Stop Promoting Your Top ICs: “When They Win, You Win.” Lessons for Modern ManagersModern product orgs live or die by the quality of their managers. I break down the most useful ideas from “When They Win, You Win.”, including how to avoid the common mistake of promoting top ICs without assessing real leadership behaviors. You’ll learn the key signals that predict manager readiness, interview prompts to suss out…
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From PM to VP: Proven Tactics to Accelerate Your Product Career and Lead with Confidence
Read more: From PM to VP: Proven Tactics to Accelerate Your Product Career and Lead with ConfidenceI break down the product career into three phases: contributing as a PM, managing PMs, and leading the function. Drawing on Jiaona Zhang’s journey — from Dropbox and Airbnb to VP of Product at Webflow — I share practical guidance you can apply today. Learn how to choose PM roles that compound learning, avoid early…
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Why the COO Role Is the C-Suite’s Most Fluid: Archetypes, No-Blame Culture, and CEO Guidance
Read more: Why the COO Role Is the C-Suite’s Most Fluid: Archetypes, No-Blame Culture, and CEO GuidanceThe COO role is uniquely fluid—and that’s its power. I reflect on lessons informed by leaders like Sara Clemens, most recently COO of Twitch and former COO of Pandora, and break down what to cover: COO archetypes, good strategy, no-blame culture, and “decision rights.” You’ll learn how to align outcomes vs output, institutionalize blameless learning,…
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