The demand-supply gap for senior product leaders reached critical levels

In cricket, there is a concept called the genuine all-rounder. Not someone who bowls a bit and bats at number eight. A genuine all-rounder: someone who would make the team as a specialist in either discipline. Think Jacques Kallis or Ben Stokes. The cricket world produces perhaps three or four of them per generation. Thousands of professional cricketers play the game at any given time. But the ones who are genuinely elite at two fundamentally different skills can be counted on one hand.

The product industry has an all-rounder problem of its own. And it is getting worse.

The eleven-month search

At Adobe, I watched a VP of Product search stretch across eleven months. Eleven months of recruiter calls, interview panels, case study presentations, and reference checks. The role was well-defined, the compensation was strong, and the company's reputation was not the issue. The issue was simpler and more stubborn than any of those things.

The candidates with deep enterprise experience could run a product organisation. They knew how to manage stakeholders across business units, build roadmaps that satisfied twelve different internal constituencies, and operate within the gravitational pull of a large company's politics. But when the interview panel asked them to describe how they would approach a new product from scratch, their answers sounded like process documents. They would describe the infrastructure of building without ever describing the building itself.

But the candidates with startup experience had the opposite problem. They could talk about building with an intensity that lit up the room. They had launched products from nothing, made decisions with incomplete data, and shipped on timelines that would give an enterprise PM a panic attack. But when the panel asked them how they would manage a product organisation of forty people across three time zones, their answers got vague. "I would hire great people and get out of their way" is a philosophy, not a plan.

The gap between those two skill sets was the actual bottleneck. Not compensation. Not company brand. Not location. The market simply did not have enough people who had done both.

They eventually filled the role. But the person they hired had to be convinced to leave a position they were happy in. The search cost, in recruiter fees, interview hours, and the eleven months the role sat empty, was staggering.

The dual-context leader

I have started calling this the dual-context leader: someone who has both zero-to-one experience and scale experience, and who can credibly operate in either mode. The dual-context leader is rare for structural reasons, not accidental ones.

Think about how product careers actually develop. You either start at a startup or you start at a large company. If you start at a startup, you spend your formative years learning to build from nothing. You learn to make decisions with no data, ship with no process, and wear seven hats because there is nobody else to wear them.

But if you start at a large company, you learn a completely different set of skills. You learn to build consensus across teams, manage dependencies, and influence without authority in organisations where authority is distributed across a dozen people who all think the product should go in a different direction.

The problem is that each environment actively selects against the other skill set. Startups reward speed and autonomy. Large companies reward collaboration and process. The person who thrives in one environment often struggles in the other, not because they lack talent, but because their instincts are calibrated for a different game.

Building from nothing and scaling within complexity are different sports played on different fields. The market wants someone who has won at both.

The specialisation trap

This creates what I think of as the specialisation trap. The longer you stay in one context, the more specialised your instincts become, and the less equipped you are to cross over.

I have lived this tension in my own career. My early years were spent in startup environments, where building from zero was the only mode that existed. At my first startup, we did not have roadmaps. We had arguments at a whiteboard and a shared sense of urgency. The feedback loop was immediate: build something, ship it, watch users react, adjust. That speed became addictive.

But then I moved into enterprise environments. At Boeing, the feedback loop was measured in months, sometimes years. The users were aircraft maintenance crews working in conditions I had never imagined until I visited a hangar. At Adobe, a single product decision could ripple across teams I had never met. The skills I needed were patience, political awareness, and the ability to build alignment across people who had fundamentally different incentives.

I am not telling this story to suggest my career path was some kind of brilliant strategy. It was mostly accidental. But I recognise now that the combination of those experiences is genuinely uncommon. Most product people I know have deep expertise in one context and surface-level familiarity with the other. The ones who have real depth in both can fill a small room.

The specialisation trap is self-reinforcing. Companies hire for the experience they need right now. A scaling company wants someone who has scaled. A startup wants someone who has built from nothing. Nobody posts a job listing that says "we need someone who has done both, and we are willing to wait a year to find them." But that is exactly what they end up doing.

What $300,000 cannot buy

Average compensation for VP of Product has crossed $300,000 in the US. That number is not the problem. Companies are willing to pay. The problem is that money cannot manufacture the career path that produces a dual-context leader.

The most expensive hire a company will ever make is the senior leader they settle for because the right one does not exist yet.

I have watched companies make that compromise. They hire the enterprise operator and hope she will develop the builder's instinct. Or they hire the startup founder and hope he will learn organisational complexity. Sometimes it works. More often, it creates a painful eighteen months where the leader struggles with half the job while the organisation absorbs the cost.

But the alternative is worse. Leaving the role empty for a year means the product organisation drifts. Decisions get made by committee. The best ICs on the team start looking at other opportunities because nobody is fighting for their growth.

There is no clean solution. The gap exists because the industry has not figured out how to systematically create the career path that produces a dual-context leader.

The accidental path

The few dual-context leaders I have met all have one thing in common: their career paths look messy on paper. They jumped between startups and large companies. They took roles that seemed like lateral moves at the time.

But those messy paths are what produced the range. You cannot develop zero-to-one instincts inside a large company. You cannot develop organisational complexity instincts inside a startup. The only way to get both is to cross between the two worlds, and that crossing always looks inefficient from the outside.

The industry talks about this gap as a hiring problem. It is not a hiring problem. It is a career design problem. And until we build product career paths that intentionally create movement between building and scaling environments, the gap will keep widening.

The people who close it will not be the ones who optimised for a clean resume. They will be the ones whose careers look like a series of bets that only make sense in retrospect.