Every week, a quiet but powerful reshuffling happens across boardrooms and C-suites—and unless you’re paying close attention, it’s easy to miss what these moves signal.

In the May 21st issue of DirectorMoves, dozens of new directors were appointed, CEOs were named and seasoned executives stepped down. For the most, these might seem like ordinary leadership changes, but at Chilmark Advisors, where we specialize in helping executives access the hidden market of board and leadership opportunities, these updates offer more than surface-level news, they reveal deeper trends shaping the leadership landscape. One trend is clear, companies are actively rethinking who gets a seat at the table and why.

Take Capital One, for example. As part of its acquisition of Discover Financial, it appointed Jennifer Wong, Thomas Maheras, and Michael Shepherd to its board. Wong, the current COO of Reddit, represents the rising demand for digital fluency and operational savvy in legacy financial institutions.

Similarly, Bath & Body Works just brought on Dan Heaf, a former Nike strategist, as CEO and director—an unmistakable signal that transformation experience is no longer optional, it’s foundational. Behind each appointment is a strategic calculation.

These companies aren’t just filling vacancies, they’re shaping the future of their leadership to meet the moment. But here’s where it gets interesting: many of these board seats weren’t filled through public searches or high-profile listings. Instead, they likely emerged through networks, targeted outreach and direct introductions, the very heart of the hidden market that our team has built, to help clients access.

While companies reshuffle, the numbers still tell a sobering story. Since January, 77 women have exited board seats compared to 137 men. But among boards of companies, with over $5B in market cap, women have only gained two net new seats. That gap isn’t just about representation—it’s about opportunity pipelines that remain too narrow and often too opaque.

At Chilmark Advisors, we use what we call the reverse search philosophy: instead of waiting for roles to be posted, we help candidates identify the decision-makers, most aligned with their skills, craft targeted outreach and build momentum through direct follow-ups. The traditional job market isn’t where leadership roles are decided. That happens through relationships, timing and visibility. Leadership transitions, like those in DirectorMoves, remind us that the right time to raise your hand isn’t when a job is posted, it’s well before that, when priorities are shifting and possibilities are quietly opening. If you’re an executive or aspiring board member looking to understand or access this space, our message is simple: you don’t have to wait for the right door to open. Sometimes, you just need to knock on the right one.