Finding AI-Adept CEOs:
What Sponsors Need to Know
The CEO profile in private equity -backed software is being rewritten in real time. AI fluency, product orientation, and the ability to lead through transformation have replaced the traditional operator playbook.
In this Tailored Talent panel discussion, Bespoke Partners CEO Eric Walczykowski sits down with Katherine Baker, Jenny Gray, and Alex Bossetta, the leaders of the CEO, Board and P&L practice, to talk through what sponsors are looking for, why the talent market is tighter than ever, and what it takes to land an AI-adept CEO in 2026.
Recruiting AI-Adept Leaders
Best Practices Guide
NEW: 2Q 2026 Update
- How AI is reshaping organizations, operating models, and leadership expectation
- What "AI-adept" means across leadership roles
- How to assess AI literacy
- Assessment guides & sponsor checklists for AI leadership recruiting
featured speakers
The SaaS landscape is shifting faster than most private equity -backed software companies can adapt.
AI is reshaping every product roadmap, every go-to-market motion, and every leadership expectation. The CEO who worked five years ago may not be the CEO who creates value today.
In this Tailored Talent panel discussion, Bespoke Partners CEO Eric Walczykowski brings together the firm's CEO, Board and P&L practice leaders for a candid conversation on what is changing in the executive market and how the best sponsors are responding.
Katherine Baker, Partner and CEO Practice Lead, Jenny Gray, Partner and CEO Practice Expert, and Alex Bossetta, Partner and CEO Practice Expert, cover the full landscape: the rise of the product-leaning CEO, how AI fluency is being assessed when there are no 30-year resumes to lean on, why there are roughly 100 executives in the world who have run a software company above 500 million in revenue, and what sponsors need to do differently to land the right leader in a market where the best candidates are fielding 20 to 30 calls in the first two weeks after a deal is announced.
This is the conversation happening inside the most active CEO search practice in private equity-backed software. Bespoke Partners has placed more CEOs in PE-backed software than any other firm in the world. What the team shares here reflects what they are seeing on the ground every day.
“If you are thinking about changing your CEO, act on it sooner rather than later.”
Your full-spectrum human capital partner
Bespoke Partners is the leading software executive search firm and the top private equity recruiter. We have transformed hundreds of companies with our recruiting expertise in: CEOs, CFOs, CROs, CMOs, CSOs, CCOs, CCSOs, CHROs, CPOs, CTOs, CIOs, CISOs, VPs of Engineering, VPs of Marketing, VPs of Sales, VPs of Product, VPs of Customer Success, VPs of HR, VPs of Operations, Controllers, VPs of FP&A, Presidents, GMs, Board Members, Operating Partners and many more.