Hello Reader,
I want to talk about the step up into product leadership, because it's the transition I get asked about most, and it's the one almost everyone underestimates. I did too.
Here's the uncomfortable truth: the skills that made you a great Product Manager, and then a great VP of Product, are not the skills that will make you a great product executive. Most people find that out the expensive way.
Every step up this ladder is steeper than it looks. As an individual contributor, the job is about getting things done. You know your market, you exercise good product judgment, and you ship the right things for your product. The move to VP stretches that: now you're expanding your scope across multiple products and organizing a team of product managers around them, coaching others to make the calls you used to make yourself.
That's a real jump, and plenty of people stumble on it. But notice what stays constant. At both levels, you're still measured on your product judgment, and when something breaks, you can usually reach in and fix it yourself.
The leap to the executive seat is greater than either of those, because that constant finally breaks. Suddenly the levers you're used to pulling aren't connected to anything. You can't personally fix twelve teams. What you can change is the system those teams work inside: how strategy gets set and communicated, how teams get designed and funded, what practices are expected, and what leadership actually rewards.
That's the real transition. You go from managing products to designing the system that produces good product decisions. And the piece of that system people underestimate most? Strategy.
AI is raising the stakes on all of this faster than anything I've seen. Your teams can now build and ship more in a quarter than they used to in a year. That sounds like a gift, and it is one... if the system around them is pointing all that new capacity at the right problems. If it isn't, nothing dramatic happens. The releases go out, the demos look great, and the returns quietly never show up. Shipping fast without a strategy fails silently. You only find out when the ROI is missing, and by then you've spent a year of that new speed building things nobody needed.
Strategy is now your primary product
At the team level, strategy is something you receive and translate. At the executive level, strategy is something you create — and here's the part that gets missed — something you have to deploy.
Try this test. Ask five product managers, in five different parts of the business, to draw the line from what they're working on right now to the strategic bet it supports. Can they do it? Can they explain the business reasons behind their work?
When they can't, it's usually not a talent problem. Your strategy might be genuinely good. It might just not be translating into something teams can actually act on, or it's written so broadly that everything qualifies as supporting it, so every team invents their own interpretation and hopes for the best. Either way, your strategy exists as a document without existing as shared understanding.
Why does this matter so much? Because deployed strategy is what lets people prioritize without you. When teams genuinely understand where the company is going and how their piece connects, they can make aligned decisions at their own level and say no to work that doesn't fit. When they don't, prioritization defaults to whoever is loudest in the room, and you'll feel it as a thousand small escalations landing on your desk.
That was always true. But AI has changed the cost of getting it wrong. When building was slow, a team pointed at the wrong problem wasted a quarter. Now they can ship their way deep into the wrong problem before anyone thinks to ask why. Building isn't the bottleneck anymore in most product organizations. Deciding what's worth building is, and that decision quality depends directly on how well you've deployed the strategy.
Your strategy lives in your funding model
Here's something I wrote on LinkedIn recently that seems to have hit a nerve:
The most consequential product decision you make as an executive is not on the roadmap. It's in the funding model.
We spend enormous energy negotiating what goes into the next quarter, and almost no energy on the mechanism that decides how money and people get committed in the first place. That mechanism is quietly setting the ceiling on everything else you're trying to do, including your strategy. You can write the sharpest strategy in the world, but if your budget process funds projects and features, your company's actual strategy is whatever got funded in November.
Think about what an annual, project-based budget really asks of your teams. It asks them to commit to a solution before they have the information to know whether it's the right one. It funds a set of features rather than a problem worth solving. So the moment a team learns their approach isn't working, the honest response — stop, and redirect the money — is the one thing the budget cycle can't accommodate. And then we act surprised when teams ship what they promised instead of what customers needed.
Want to watch this play out in real time? Look at how most companies are funding AI right now. Enormous annual commitments to named AI initiatives, scoped like projects, with a promised solution attached, committed before anyone knows whether it's the right one. Those are exactly the bets that most need room to change course, because nobody's first idea about where AI creates value in their business survives contact with customers. A project budget can't accommodate that learning, which is a big part of why so many companies are about to discover their AI spending as a line item with no returns next to it.
The fixes aren't crazy, but they're also not simple to implement in large organizations. Fund outcomes and standing teams rather than projects. What does that mean? Think of funding in tranches. Give innovation bets (and your AI bets belong in this category) a stage-gated funding path so a two-year idea doesn't get killed by a one-quarter revenue target. Keep teams stable long enough to build real context in their domain, and staff them for what their mission actually requires instead of a standard template.
But notice who those conversations are with. Every one of those changes requires a conversation with your CFO and your CEO, not with your engineering leads. It also means making sure the incentives for the other leaders around the table are aligned, because a strategy your peers are incentivized to undermine won't survive contact with the next planning cycle.
That's what catches most new product executives by surprise. Half the job is building relationships with the CEO, CFO, and CTO so you can change the structural conditions your teams are operating inside. And nobody trains you for that half. There's a mountain of material on how to be a good product manager, and almost nothing on how to run a product organization from the executive seat.
My honest take on the moment we're in: AI is going to widen the gap between product organizations, not close it. The companies that get real returns from it will be the ones whose executives fixed the system first: the strategy deployment, the funding model, the executive partnerships. The speed is available to everyone now. The system that points it somewhere valuable is not.
Closing that gap is exactly why I built the CPO Accelerator. It's a live program, taught by me, in a deliberately small cohort of product executives from around the world. We cover product strategy at the company level, organizational and team design, the funding and governance model, product operations, and building the executive partnerships with your CEO, CFO, and CTO that make all of it possible - all worked through against the real situations participants bring in.
It's for sitting CPOs, first-time CPOs in their first year, and VPs or SVPs of Product who can see the executive seat coming. And plenty of people join without wanting the CPO title at all, because they need to think and communicate like one to be effective where they already are.
Applications for the October cohort close in five days, on September 15.
Apply for the October cohort →
If you're on the fence or not sure it's the right fit for where you are, just reply to this email. I read these.