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AI, CPTOs, and Risk Aversion: What’s Driving Product & Tech Hires in 2025?
by Ryan Bonner
As we navigate 2025, the executive hiring landscape for product and technology leaders is being shaped by significant forces — from the expanding role of AI to increasing risk sensitivity and changing compensation dynamics. In a recent Tailored Talent episode, I sat down with our CEO, Eric Walzakowski, to unpack what we’re seeing on the ground across dozens of searches and strategy sessions with clients.
Here are some of the most important insights from that conversation — and what they mean for private equity-backed software companies building and evolving their leadership teams.
What We're Seeing Across 70+ Product & Tech Searches Per Year
Our team executes 70–80 searches per year across CTOs, CPTOs, VPs, and SVPs of product and engineering. That scale gives us a meaningful vantage point into where the market is moving — not just in who’s being hired, but how companies are thinking about structure, succession, and long-term fit.
Here’s what we’re seeing:
Counteroffers are back in a big way. [...] We've had candidates say, “I won’t take a counter.” And then they see the offer — and they’re surprised.
Step-Up Talent: Betting on the Next Generation of Leaders
Many of our clients are looking not only for current C-suite leaders, but for VPs and SVPs who are ready to step into the top role in a fast-scaling environment. With the help of the Executive Index, we’re able to uncover and assess these "step-up" candidates — those with the ambition, capabilities, and trajectory to grow into transformational leaders.
We’ve had considerable success placing these future-ready executives — and helping our clients build long-term bench strength in the process.
CTOs on the Rise, But CPTOs Are the Future
2024 brought an unusual shift: CTOs outpaced CPOs in demand, particularly in changeovers within portfolio companies. This was notable because, historically, product leadership has been the first lever pulled when strategy changes. But with AI and ML fundamentally reshaping how organizations operate and deliver, technical leadership took center stage.
That said, we’re seeing demand for product leadership rebound in 2025 — and increasingly, clients are exploring the Chief Product & Technology Officer (CPTO) model. In roughly 30–40% of our current engagements, clients are asking: Do we need both roles? Or can one leader drive a cohesive vision across both domains?
This hybrid role often becomes a developer of strategy and teams — bringing cohesion to two functions that need to scale in tandem.
Navigating a Healthy Level of Risk Aversion — and the Return of the Counteroffer
Executives are showing a healthy level of risk aversion in the current market — and that’s a perfectly rational response to macro uncertainty. To pull someone great out of a good role today, the opportunity needs to be compelling across multiple dimensions: role, company trajectory, culture, compensation, and leadership alignment.
And even then, counteroffers are back in a big way.
In our episode, Eric shared a story of a CEO placement that involved an 18-month severance package and a buyout of the executive’s equity loan from their current company — a bold but well-informed move based on our market data. The result? The counteroffer became irrelevant.
We've had candidates say, “I won’t take a counter.” And then they see the offer — and they’re surprised. The size and seriousness of these offers often force hard conversations late in the process. That’s why we help clients structure offers with precision, anticipate objections, and understand that closing top talent today often takes more than just a compelling role.
Compensation Trends: Steady Averages, Strategic Outliers
Compensation for product and tech executives in private equity remains relatively steady — but there are some key nuances.
As I told Eric, we are playing in the private equity world where everyone knows that annual cash payment is not what we’re working hard for. It’s the exit event. That’s why the multiple on cash through equity remains a critical component, often in the 7–9x range. At the same time, we’re seeing more anomalies at the high end — cases where standout candidates with multiple offers are commanding both higher cash and stronger equity packages. These are often executives with proven track records in scaling, exits, or transformational change — and they have leverage. We help our clients understand when it’s worth it, and how to win those leaders the right way.
What 80% of Our Scorecards Have Included in 2025
AI and ML continue to dominate the strategic roadmap and they’re now appearing in over 80% of the scorecards we’ve seen in 2025.
What’s particularly interesting is how AI is being applied. Yes, there are companies pursuing innovation through AI— entering new markets, building new products, or expanding their footprint. But we’re also seeing a major emphasis on efficiency — using AI to improve margin, scale customer delivery, and reduce headcount growth while growing revenue.
As a result, we’re seeing increased demand for leaders who understand how to build AI-aligned org structures, integrate AI capabilities into existing workflows, and lead teams through transformation. That’s a very different skill set from someone building a product 100% from scratch.
Final Thoughts: Building for the Long Term
One of the most meaningful parts of our work is helping clients understand when a search is the right move — and when it’s not. As Eric put it on the podcast, “Sometimes the right thing to do is nothing. And sometimes it’s to reframe the problem.”
That’s where tools like the Executive Index become so valuable. It’s not just about surfacing the right candidates faster — it’s about helping our clients gain clarity and confidence. In some cases, it confirms that the market is deep enough to move forward. In others, it reveals that a narrowly scoped search may not yield what’s needed — sparking bigger conversations about role design, location flexibility, or org structure.
We’ve even had clients adjust strategy based on insights like airport mapping, which shows which executives are within a one-hour direct flight of a given location. Those kinds of details — rooted in data and experience — support smarter decisions, whether a search proceeds or not.
At the end of the day, leadership decisions carry long-term impact. Our role is to help clients make them with precision, transparency, and the full picture in front of them.
To learn more about leadership trends in product and technology, subscribe to the Tailored Talent podcast or connect with the Product & Tech team at Bespoke Partners.
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