Author Archives

Danielle Iera

The CEO Leadership Market Is Tightening as AI Raises the Stakes

By Billy Chapman | July 13, 2026

Private equity-backed software and SaaS companies are entering a new leadership cycle. While deal activity remains uneven and sponsors continue to navigate a cautious investment environment, AI is rapidly reshaping operational expectations and value creation priorities. At the same time, competition for proven CEOs is intensifying.

The Next 2–3 Years Will Belong to AI-Ready Leadership Teams

By Billy Chapman | May 27, 2026

Increasingly, CEOs are taking a more rigorous and forward-looking approach to assessing their leadership teams. The question is no longer whether the team has performed, but whether it is built for the next phase of the business.

Seizing the Talent Advantage: Early Strategies for Portfolio Success in 2025

By Billy Chapman | January 30, 2025

In today’s cutthroat market, talent acquisition remains the kingmaker of portfolio performance. With M&A expected to surge in 2025, the race to secure exceptional executive leadership will separate the winners from the rest of the pack.

Billy Chapman

Billy Chapman

Billy is a Vice President on the Private Equity Partnerships team at Bespoke. Based in San Francisco, he joined the firm in April 2024. Prior to Bespoke, he worked for YipitData in Business Development where he provided data-driven research reports and insights to large investment funds.

Billy also spent nearly six years at Adobe in the Document Cloud and AdCloud businesses in the sales organization and built-up institutional knowledge of how Enterprise Software companies operate.

Billy has his B.A. in Economics from Middlebury College, where he was captain of the Football and Lacrosse teams and was an All American over the course of 3 seasons.