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Mastering AI Debugging: From Data Leakage to Evals—Practical Tactics I Use in the Wild
Read more: Mastering AI Debugging: From Data Leakage to Evals—Practical Tactics I Use in the WildIf you’ve ever wondered how to know whether your AI product is truly any good, this reflection distills a proven approach to debugging and evaluation. I share how to catch data leakage early, when to use code-based assertions versus LLM-as-judge, and why your CI/CD must include broken cases. You’ll learn how to use synthetic data…
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Deliberate Practice for Product Teams: How AI and On‑Demand Learning Unlock Mastery
Read more: Deliberate Practice for Product Teams: How AI and On‑Demand Learning Unlock MasteryDeliberate practice is the missing link between product learning and lasting behavior change. In this episode recap, I share why a blended model—cohort-based structure plus on-demand practice—delivers both rigor and flexibility for product teams. I highlight how AI-powered interview coaches and microlearning formats provide expert-quality feedback and more high-quality reps without losing the human element.…
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AI and Customer Interview Synthesis: Speed Up Insights Without Losing Empathy
Read more: AI and Customer Interview Synthesis: Speed Up Insights Without Losing EmpathyWeekly customer interviews can create a mountain of transcripts—and a temptation to let AI do the synthesis. I explain exactly where AI helps, where it hurts, and how to structure synthesis so insights stay actionable. You’ll learn why single-interview synthesis must come before cross-interview themes, how to prevent empathy loss and skill atrophy, and how…
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Inside Alyx: Dogfooding, Evals, and Observability That Power an Agentic AI Future
Read more: Inside Alyx: Dogfooding, Evals, and Observability That Power an Agentic AI FutureThis is a pragmatic, first-hand look at how Alyx was built by dogfooding Arize’s own platform—moving from messy notebooks to a disciplined eval and observability stack. You’ll see how tracing, tool design, and cross-functional workflows make GenAI agents reliable and improvable. The discussion covers how customer success engineers surfaced repeatable workflows and why early skills…
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How to Design Your Product Leadership Legacy: Impact, Craft, and Values That Endure
Read more: How to Design Your Product Leadership Legacy: Impact, Craft, and Values That EndureThis reflection-driven episode challenged me to define the product leadership legacy I’m actively building—today, not someday. I share how I reframe “legacy” into actionable questions for Q4 planning, and why I balance impact with craft to create durable results. You’ll see how personal brand and values shape what colleagues remember when the stakes are high.…
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AI Coworkers That Actually Work: Inside Neople’s Guardrails, Evals, and Customer-Ready Agents
Read more: AI Coworkers That Actually Work: Inside Neople’s Guardrails, Evals, and Customer-Ready AgentsI explore how Neople builds “digital coworkers” that blend automation reliability with AI flexibility to handle real customer work. You’ll see how the team balances code, agents, and guardrails, and why production evals are crucial for catching hallucinations before they reach customers. I share why teaching non-technical users to build automations conversationally accelerates adoption and…
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From Closet Cold Calls to Category Leader: Gusto’s Playbook for Urgent Product-Market Fit
Read more: From Closet Cold Calls to Category Leader: Gusto’s Playbook for Urgent Product-Market FitI break down how Gusto turned a burning SMB problem into a platform by prioritizing emotional urgency over polite feedback and embracing rejection as a discovery tool. You’ll see why “It’s not an MVP, it’s something that wows people” is essential in high-stakes workflows like payroll and taxes. I highlight hiring for humility, the weekly…
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How Braintrust Nailed Product-Market Fit: Paranoia, Patience, and High-Bar Quality
Read more: How Braintrust Nailed Product-Market Fit: Paranoia, Patience, and High-Bar QualityBraintrust’s playbook for product-market fit in GenAI pairs a relentless quality bar with deliberate go-to-market restraint. By transforming evaluation pain into an end-to-end platform for building AI apps, they earned pull from high-bar users instead of pushing features. The evolution of a governed prompt playground, forward deployed engineers, and rigorous evals turned demos into durable…
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Inside a $15B Autonomy Powerhouse: Founder Grit, Multi-Product Strategy, and GTM Wins
Read more: Inside a $15B Autonomy Powerhouse: Founder Grit, Multi-Product Strategy, and GTM WinsI break down how Applied Intuition scaled a vehicle intelligence platform to a $15B valuation and why its playbook matters for PM leaders. You’ll learn why two underrated founder traits—stamina and operational discipline—compound into execution speed. I share practical ways to unlock 1–3 extra months of productivity each year without burnout. We’ll cover product-led GTM…
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How Ignoring Silicon Valley Advice Fueled a $3B Fintech Breakout—Lessons I Apply Daily
Read more: How Ignoring Silicon Valley Advice Fueled a $3B Fintech Breakout—Lessons I Apply DailyI don’t copy-paste Silicon Valley advice, and this fintech case study proves why. In this first-person breakdown, I share what strong product-market fit actually feels like, how to avoid the weak PMF trap, and why “personality trumps culture playbooks.” You’ll learn a practical hiring system for cultural fit, a framework for evaluating scalable ideas, and…
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Inside the AI‑First Web: Designing Agent‑Friendly APIs, Prioritizing Accuracy, and Scaling Trust
Read more: Inside the AI‑First Web: Designing Agent‑Friendly APIs, Prioritizing Accuracy, and Scaling TrustAI is becoming the web’s second user, and that reality changes how we design, measure, and monetize our products. I break down why accuracy must beat speed for deep research use cases and how agent-friendly APIs create trust and composability. You’ll learn how to evolve your ICP as reliability improves, when to launch based on…
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Inside Canva’s $42B Rise: Unconventional Growth Levers, Onboarding Wins, and PM Lessons
Read more: Inside Canva’s $42B Rise: Unconventional Growth Levers, Onboarding Wins, and PM LessonsCanva’s journey from a bold idea to a $42B platform offers a masterclass in product-led growth. I unpack how smart persona selection, intuitive onboarding, and community-led distribution helped the product resonate with people who thought they would never design anything. You’ll learn why launch day is the start of learning, not the finish line, and…
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