May 22, 2025 · 4 min read
There's a running joke among my peers in product leadership roles. It goes something like this: you join a company as the new CPO, you try to deliver some meaningful impact, and then you brace yourself for the inevitable exit within a couple of years. It’s a cynical take, but it’s rooted in a difficult truth: the role of the product leader is uniquely precarious.
Why is it so hard to succeed and endure as a product executive? From my experience and conversations with other leaders, the reasons are rarely a mystery. Failure isn't random; it tends to follow one of three predictable paths.
The most common failure mode, especially at earlier-stage companies, is a fundamental misalignment on who truly owns the product vision. No one tells you this in the interview, but nine times out of ten, the founder-CEO still sees themselves as the primary product visionary.
The hiring process often masks this reality. The founder and the CPO candidate will have exciting, high-level jam sessions about the future of the product. The candidate leaves feeling empowered and aligned, believing they've been hired to set the strategic direction. The founder leaves feeling they've found a great partner to help them execute their vision.
This "vision impasse" creates a deep-seated friction that eventually becomes untenable. The CPO pushes for a new direction based on their research and experience, while the founder, relying on their deep-seated intuition, resists. The CPO is seen as not "getting it," and the founder is seen as a micromanager. Trust erodes, and the partnership fails.
The second path to failure is hiring a leader whose expertise doesn't match the company's current needs. The work of a product organization is not monolithic; it changes dramatically based on the company's stage and strategy. Broadly, there are four types of product work:
The problem is that many companies misdiagnose their own needs. For example, a leadership team might hire a world-class growth expert obsessed with optimizing conversion funnels, when what the business truly needs is a leader focused on building out the complex enterprise features required to move upmarket. The leader's skills, while impressive, are a mismatch for the job to be done. The result is frustration on both sides and a failure to move the metrics that matter most.
Even if you achieve a perfect match between a leader's skills and the company's needs at a single point in time, the ground is constantly shifting. This is the third and most difficult failure path: the leader's inability to adapt as the needs of the business evolve.
A company might spend two years in a "scaling PMF" phase, requiring deep feature work and iteration. Then, a market shift might demand a pivot to a "growth" phase focused on user acquisition. The skills that made a product leader successful in the first phase are not the same ones required for the second.
The traditional product leader was often a specialist in one of these areas. The modern, successful product leader must be a chameleon. Their primary skill is not just expertise in one domain, but the ability to correctly diagnose what the business needs now, and to re-weight their focus and their team's efforts accordingly. The leader who can only do one thing well will inevitably find themselves leading a team that is solving yesterday's problems.
The high failure rate for product leaders isn't an unsolvable mystery. It's the predictable result of misalignment on vision, a mismatch of skills, or an inability to adapt to change. Avoiding these traps requires a level of explicit communication and self-awareness from both the CEO and the CPO that is often lacking in the hiring process.
Ultimately, the product leader's role is to be what the business needs them to be at any given moment. The leaders who not only survive but thrive are the ones who master this art of diagnosis and adaptation, guiding their organizations through the inevitable evolution of a growing company.