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How CEOs Are Thinking About Their Next Act: Timing, Risk, and Conviction in 2026
by Eric Walczykowski, Katherine Baker
The CEO market heading into 2026 is not just tight. It is selective.
Exit paths are reopening, deal activity is accelerating, and demand for proven leadership remains high. At the same time, many experienced P&L leaders are staying put, evaluating opportunities through a far more deliberate lens than in prior cycles.
In a recent Tailored Talent conversation, I sat down with Katherine Baker, CEO, Board and P&L Recruiting Practice Lead at Bespoke Partners, to unpack what is actually shaping CEO decision-making right now. What stood out was not just the constraint in the market, but the degree of nuance executives are applying as they think about what comes next.
This is increasingly a market defined by conviction, not volume.
Why the CEO Market Remains Constrained
Two forces continue to collide. On the demand side, sponsors are reassessing leadership as exits come back into view and new platforms are created. On the supply side, many proven CEOs are choosing to stay through exit, strengthening their track record and maximizing wealth creation before considering another move.
The result is straightforward: Demand is rising faster than supply.
Bespoke Partners has completed nearly 70 CEO searches over the past two years, with more than 350 CEO searches overall. That volume provides real-time visibility into just how constrained the market has become and why traditional recruiting assumptions are breaking down.
The Career Arc Executives are Optimizing for
One of the most overlooked dynamics in CEO recruiting is time.
Executives do not view opportunities as interchangeable. Many are thinking in terms of one or two remaining meaningful turns, not an open-ended series of moves. That reality fundamentally changes how they evaluate risk, sponsor quality, and exit timelines.
We increasingly see executives willing to make tradeoffs, even on near-term cash, to align with a sponsor or platform that positions their final chapter at a higher level. When sponsors and search partners fail to account for career arc and life stage, credibility erodes quickly.
Understanding where a leader is in their career is often what determines whether they take the call at all.
Compensation is Evaluated Through Risk and Realism
Compensation pressure across the CEO market continues to rise, but headline numbers rarely tell the full story.
Across the market today:
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Average CEO cash compensation is clustering around $600K for businesses under $50M in ARR
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Cash frequently exceeds $1M to $2M for businesses above $1B in revenue
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Equity value expectations commonly range from $12M to $15M at exit for sub-$50M platforms
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$20M or more is increasingly common as scale increases
What matters most is how that value is structured, the probability of achieving it, and the time required to get there.
Executives are evaluating compensation through the lens of risk, timing, and downside protection, not just upside potential.
Creativity Has Become Table Stakes
Standard packages are often no longer sufficient.
We are seeing sponsors deploy more creative structures to attract and secure proven CEOs, particularly in sectors that have experienced volatility. These include paying off legacy executive loans, guaranteed RSUs used as downside protection, and hybrid equity structures designed to better balance risk.
In one recent placement, a CEO entered a $100M business with approximately $5M in day-one downside protection and close to $17M in potential upside. These approaches are no longer edge cases. They are becoming necessary tools in competitive searches.
How Equity Value is Really Assessed
A common misconception in CEO recruiting is the fixation on ownership percentage.
- No two cap tables are created equally.
- Performance thresholds vary.
- Time horizons differ.
- Exit assumptions are rarely uniform.
Our approach reframes equity by modeling expected exit value, dividing by anticipated hold period, and translating that outcome into an annualized view of equity compensation. Making $10M in two years is fundamentally different than making $10M in five.
Sophisticated executives understand this distinction, and alignment here often determines whether a deal closes.
Transparency is the Gating Factor
Executives today have real optionality, and with that comes less tolerance for ambiguity.
When leaders sense disorganization, unclear economics, or lack of transparency, they do not negotiate. They disengage. Clear messaging, early alignment, and credible data are no longer differentiators. They are baseline expectations.
This is why visibility into the full CEO market, paired with disciplined process and real compensation insight, is critical as we move into 2026.
The Real Question Heading Into 2026
The CEO market is not just tight. It is unforgiving.
Success will belong to sponsors who understand executive motivation, respect career timing, and communicate value with precision. It will also belong to those who partner with firms capable of seeing the entire market and converting interest into commitment.
That is how CEOs are thinking about their next act.
To learn more about CEO, Board, and P&L leadership trends, subscribe to the Tailored Talent podcast or connect with the CEO, Board and P&L recruiting team at Bespoke Partners.
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