organizational development
- AI Strategy (315)
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- Product Management Leadership (306)
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The Organizational Infrastructure Responsible AI Actually Needs
A practical operating model for assigning AI ownership, limiting agent authority, funding human oversight, and turning failures into safer systems.
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How to Roll Out AI Without Dodging the Job Security Question
A practical playbook for making credible job commitments, testing AI on business outcomes, and showing employees how their roles will change.
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How to Lead When AI Expands Roles Before Titles Change
A practical operating model for using AI across functional boundaries without blurring accountability, review, or specialist ownership.
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Operating Lessons from Plaid’s COO for Scaling Through Change
Plaid COO Eric Sager’s operating approach shows how capacity, customer ownership, decision trade-offs, delegation, and onboarding can support resilient growth.
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Stop Forcing Organizational Change: How I Create Impactful Product Habits Without Burnout
Organizational change is exhausting—so stop trying to force it. I focus on conditions that make change inevitable: leadership-level pain, real urgency, and awareness of credible alternatives.…
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Broken Procurement Is Costing You Talent: A Product Leader’s Playbook for Speed and Sanity
Procurement should accelerate value, not block it. In this episode recap and analysis, I unpack how sprawling forms, overreaching security reviews, and unclear ownership repel the…
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Unlocking AI Agents: The Real Barrier Is Readiness—Not Capability—Here’s How to Scale
The biggest barrier to scaling AI Agents isn’t model capability—it’s organizational readiness. I break readiness into five types (content, scope, procedural, data, execution) and show why…
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Figma’s Executive Scaling Playbook for IPO Readiness
A practical operating model for growing executives, installing public-company discipline early, and aligning product, finance, and AI investment.
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Beyond Command and Control: How I Build Trust, Speed, and Autonomy in Product Teams
Uncertainty tempts leaders to tighten control, but that speed is often a mirage in complex product environments. I explain why no single leader can hold all…
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From 70 Employees to Dominance: My Playbook for Hypergrowth, Focus, and Top-Down Goals
Scaling an atoms-based marketplace demands a different kind of product leadership. In this first-person playbook, I share how I apply a simple “plate spinning” framework to…
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Product Work Is Relationship Work: How I Align Stakeholders Faster and Cut Team Politics
AI can speed up delivery, but it can’t replace the human work of product management: aligning stakeholders, navigating competing incentives, and creating shared understanding. In this…
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Inside the Most Politically Dangerous C‑Suite Role: Hard Truths on Culture, Layoffs, and Leadership
Culture isn’t a perk—it’s a product. In this first-person reflection on the most politically charged seat in the C‑suite, I share why HR must think like…
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From Engineer to CEO: Hard-Won Lessons on GTM, Cloud-First Bets, and Must-Do Focus
Becoming a CEO from an engineering or product track requires an almost entirely new skillset—and a new operating system. In this reflection, I break down the…
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Staying Sane as a Product Leader: Practical Strategies I’m Using from Teresa Torres & Petra Wille
Feeling overwhelmed is rational in a world of infinite inputs and finite attention. I’m applying small, values-driven actions—guided by “Something is better than nothing”—to stay grounded…
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Inside Zipline’s Wild Pivot: My Take on Hiring Heat-Seekers and Scaling to 5,000 Hospitals
Zipline’s arc—from near-dead robotics to drone blood delivery in Rwanda—offers a standout playbook for product leaders. I break down why hiring “heat-seeking missiles for pain” beats…
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Build a Support System That Scales: How Product Leaders Maximize Impact with Delegation and AI
Feeling stretched thin as a product leader? This reflection distills a practical playbook for scaling your impact without adding hours to your calendar. Learn why executive…
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Stop Groupthink in Hiring: Proven Product-Led Tactics to Make Faster, Fairer Decisions
Hiring isn’t broken so much as it’s often badly designed. I unpack how AI-driven application volume, sprawling interview loops, and fuzzy criteria fuel groupthink and derail…
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AI Customer Service Transformation: An Operating Playbook
A practical playbook for choosing support work to automate, redesigning human roles and handoffs, governing quality, and proving durable business value.
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AI Transformation Is an Operating Model, Not a Feature Roadmap
A practical operating model for turning scattered AI pilots into measurable outcomes, safer releases, and a faster organizational learning loop.
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2026 Support Capacity Playbook: Bold AI Automation, Smarter Staffing, Zero‑Surprise SLAs
AI is reshaping support capacity planning, and the old linear volume-to-headcount model no longer holds. I center plans on automation rate (AI Agent involvement rate ×…
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