Essays
Long-form thinking on product leadership, strategy, and organizational design.
How to Know You're Ready to Be Head of Product
Readiness for the Head of Product role is not a checklist. It is a set of capabilities, orientations, and honest self-assessments that, taken together, indicate whether you can lead a product organization through the complexity that role requires.
Metrics That Actually Matter at Head of Product Level
The metrics that matter for an individual PM are not the metrics that matter for a Head of Product. Here is how the measurement framework needs to shift — and three metrics that indicate whether a product organization is operating at the level it should be.
Why Product Culture Is More Important Than Product Frameworks
Every product organization has frameworks. The ones that consistently ship great products have something harder to copy: a culture of genuine intellectual rigor about what they are building and why.
Product Strategy Under Resource Constraints
Unlimited resources reveal poor strategy less quickly than constraints do. Building a rigorous product strategy under real resource constraints is one of the most clarifying exercises in product leadership.
When to Kill a Product Line (And How to Decide)
Knowing when to stop investing in a product line is one of the hardest and most consequential decisions a product leader makes. The signals are usually present long before the decision is made.
How to Build a 3-Year Product Narrative in SaaS
A 3-year product narrative is not a forecast. It is a theory about where your market is going, why your product is positioned to win, and what sequence of moves gets you there. Here is how to construct one that holds up under scrutiny.
From Vision to Strategy to Roadmap: Avoiding the Collapse
Vision, strategy, and roadmap are three distinct artifacts that serve three different purposes. Most organizations collapse them together — and the collapse is where execution fails.
The Decision Rights Map Every Product Organization Needs
Ambiguous decision authority is one of the most reliable sources of organizational dysfunction. A decision rights map makes authority explicit, reduces escalation overhead, and dramatically improves decision speed and quality.
How Product Leaders Should Partner with Engineering Leadership
The Head of Product and the VP/CTO relationship is one of the most consequential partnerships in a software company. Getting it right compounds. Getting it wrong is one of the most common sources of organizational dysfunction.
Designing Product Org Structures for Scale
The right product org structure is not universal — it depends on your product architecture, your growth stage, and your strategic priorities. Here is how to make the decision deliberately rather than by default.
What Changes When You Move from PM to Product Leader
The promotion to product leadership feels like a continuation of the PM role with more responsibility. It is actually a fundamentally different job — and the PMs who struggle most are the ones who do not update their mental model.
Balancing Sales Demands with Product Integrity
The tension between sales and product is one of the most persistently difficult dynamics in B2B SaaS. Resolving it does not require choosing a side — it requires designing a system that gives both sides what they need.
Feature ROI in Complex SaaS Environments
Not all features are created equal, and not all feature value is captured in simple impact scores. A financial lens on feature investment changes which work gets prioritized and why.
Customization Debt: The Silent Killer of SaaS Margins
Technical debt is visible on engineering health dashboards. Customization debt is invisible — until it shows up in your gross margin, your engineering velocity, and your inability to scale customer success.
Why B2B Product Strategy Must Be Revenue-Aware
A product strategy disconnected from revenue mechanics is a vision document, not a strategy. Understanding ARR, retention, and enterprise deal pressure changes what you build and how you prioritize it.
The Hidden Architecture of Scalable Product Organizations
The most important design decisions in a product organization are not made on org charts. They are made in the structure of information flows, decision rights, and team interfaces. Most companies never design these explicitly — and pay for it at scale.
How to Align Multi-Squad Product Execution Without Micromanaging
At a certain scale, product alignment cannot be maintained by a single PM. The challenge shifts from making good decisions to building the conditions under which good decisions get made consistently across teams.
Designing Product Feedback Loops That Actually Inform Strategy
Most product teams collect feedback. Very few build feedback systems that reliably surface the signal needed for strategic decisions. Here is the difference — and how to design one that works.
Product Is a Portfolio, Not a Backlog
Managing a backlog is a task management skill. Managing a product portfolio is a capital allocation skill. The difference determines how effectively your team's capacity translates into business outcomes.
When Engineering Velocity Drops — Is It a Product Problem?
When a team slows down, the instinct is to look at engineering. Often the root cause is upstream — in how product work is defined, scoped, and handed off. Here is how to tell the difference and what to do about it.
Delivery vs. Outcome: Why Product Teams Confuse the Two
Shipping is not succeeding. Most product teams know this in theory and ignore it in practice. Here is why the conflation persists — and what it costs.
The Anatomy of a High-Quality Product Decision
Not all product decisions are created equal. Some produce durable outcomes. Others look good in the moment and degrade over time. The difference is almost entirely in how they are made, not what is decided.
Why Most Roadmaps Fail Before They Are Built
The roadmap looks complete on paper. The team is aligned. The quarter begins. And then, slowly, it falls apart. The failure was baked in from the start — and it almost always comes down to three illusions.
From Engineering Manager to Product Strategist: A 5-Year Roadmap
The path from engineering management to product strategy leadership is one of the most valuable career moves in tech. It is also one of the least well-defined. Here is a concrete roadmap.
The Economics of B2B Product Decisions
Product decisions have economic consequences that most PMs never see clearly. Understanding the unit economics behind your product choices makes you a significantly better product leader.
Why SaaS Founders Should Care About Internal Product Systems
The quality of your internal product development system — how decisions get made, how work is structured, how feedback flows — determines your product quality ceiling. Most founders do not think about this until it is very expensive to fix.
Product Thinking Beyond the Product Team
Product thinking is not a role. It is a mode of reasoning that the best companies embed across sales, CS, engineering, and leadership. Here is what that looks like in practice.
Why "Impact" Is a Better Career Metric Than Promotion
Optimizing your career for promotion produces a specific set of behaviors — most of which make you a worse product leader. Here is what to optimize for instead.
How to Build Technical Credibility as a Non-Technical PM
You do not need to write code to be technically credible as a PM. But you do need to understand the right things — and the path there is more learnable than most people think.
Transitioning from Engineering to Product: What No One Tells You
The transition from software engineer to product manager is one of the most common career moves in tech. Most people underestimate how much of what made them good at engineering actively works against them as a PM.
PM vs. EM: Which Path Actually Gives You More Leverage?
The PM vs. EM career question is usually framed as a skills fit problem. It should be framed as a leverage problem — and the answer depends on where and how you want to create impact.
Stakeholder Management Is Architecture in Disguise
The way you structure information flow, decision rights, and accountability in an organization determines what your product can and cannot become. That is not soft skills — it is systems design.
How Engineering Managers Should Think About Product Strategy
Engineering managers who understand product strategy make better technical decisions, build stronger teams, and advance faster than those who treat it as someone else's job.
Why Most PMs Think in Features Instead of Systems
Feature thinking solves one problem at a time. Systems thinking solves problems at the root. Understanding the difference changes how you build products that last.
The Difference Between a Delivery PM and a Product Leader
Many PMs are excellent at execution but never make the transition to genuine product leadership. The gap is not a skills gap — it is a thinking gap.
How Payroll and HR Products Force You to Think in Edge Cases
Building payroll and HR software is a masterclass in edge case design. The lessons apply to any B2B product operating in high-stakes, regulated domains.
Building Features for 5 Enterprise Clients Without Destroying Your Core Product
Multi-enterprise SaaS is one of the hardest product design problems. Here is how to serve high-value customers without fragmenting your codebase or losing your product soul.
Customization vs. Product Integrity: A Decision Framework
Every B2B SaaS company eventually faces the same pressure: build a custom feature for an important customer, or hold the product line. Here is how to make that call without destroying your roadmap.
Why B2B SaaS Roadmaps Are Politically Complex
In B2B SaaS, the roadmap is not just a product artifact. It is a political object. Understanding the forces acting on it is the first step to managing them.
Why Velocity Metrics Mislead Product Leaders
Story points and sprint velocity feel like rigorous measurement. They are actually a proxy that obscures more than it reveals — and building strategy around them leads to predictable failures.
How to Run Product–Engineering Syncs Without Wasting Time
Most cross-functional meetings are structured for the wrong outcome. Here is how to redesign your product–engineering syncs to actually move work forward.
Decision Logs: The Missing Artifact in Most Product Teams
Your team is making hundreds of product decisions. Almost none of them are written down. Here is why that is a serious problem — and a lightweight system to fix it.
From Roadmap to Reality: A 3-Layer Execution Model
Most roadmaps die in the gap between strategy and sprint tickets. This three-layer model closes that gap by creating a clear translation path from "what we want" to "what gets built."
When Product Strategy Ignores Technical Debt (And What Happens Next)
Technical debt is not an engineering problem. It is a product strategy problem. And ignoring it has consequences that show up in your roadmap, not your codebase.
The Hidden Cost of Overpromising Roadmaps in B2B SaaS
Overpromising on the roadmap feels like relationship-building with customers and sales. It is actually a slow-burning fire that degrades your team, your product, and your credibility.
How to Write PRDs Engineers Actually Respect
Most product requirements documents fail not because PMs cannot write, but because they include the wrong things and omit the most important ones.
Why Most PM–Engineering Conflicts Are Structural, Not Personal
The tension between product and engineering teams is rarely about personalities. It is a design problem — and once you see it that way, it becomes solvable.