Incentive Misalignment in a Shift to Long-Term Hold

searcher profile

February 28, 2026

by a searcher from Boston University - Questrom School of Business in Boston, MA, United States

Hi Searchfunder Community, Posting anonymously for obvious reasons. I’m an operator in a traditional search-backed company, now over six years in. We’ve delivered strong top-line growth, but EBITDA hasn’t kept pace due to margin volatility. The industry is currently hot, with strategics and PE showing real interest. Given our current profile, a strategic sale at a revenue multiple feels like a logical outcome. Here’s the tension: We were structured around a traditional 5–7 year hold. Now the board is leaning toward a long-term hold strategy. Philosophically, I understand it. Financially, incentives are no longer aligned. Time based vesting is mostly complete. Performance based vesting requires a transaction. A hold could push liquidity out 10 or more years. At today’s value, a recap would fully vest management. Without one, we’re effectively being asked to commit another decade plus to earn equity we’ve already created significant value toward, or walk away with less than half of our potential ownership. That’s a tough spot. Beyond a recap, what creative solutions have others seen work? Partial liquidity? Vesting resets? Dividend participation? Structural changes? Would appreciate any perspectives or examples, public or private. Thank you.
0
14
253
Replies
14
commentor profile
Reply by an investor
from University of Oregon in Sacramento, CA, USA
@redacted‌ thanks for the tag. This misalignment happens more than people admit unfortunately, especially with double trigger vesting. Before co-founding Pioneer I was at Carta for a while and saw this exact scenario play out across a lot of cap tables. A secondary is worth exploring. It would give you and investors some liquidity now, creates a milestone event that can trigger vesting, and doesn't require a full exit. A more traditional recap works similarly as others have said as well. Our firm doesn't have predetermined hold and exit periods to avoid this inevitable clash that can otherwise happen. We optimize for ongoing yield and distributions so investors are satisfied regardless if operators hold on the company for 5 years or 20. We believe the decision stays with the operator, not the investor. Tough spot, but hope you find a path forward. Happy to help anyway I can.
commentor profile
Reply by an investor
from Wesleyan University in Dedham, MA, USA
Realize, just getting your POV here, not the board/investor's, but from what you're telling, they are putting you in an unfair position. If I were an investor, I would want you to get some real liquidity now before asking you to commit for another ten years, along with your team. There are a bunch of ways of doing that. I honestly would take up ^redacted‌ on his offer above to help as he is perhaps the leading expert in these situations. You could also speak to some of the follow on vehicles at PL and other places just to get an idea of what a recap looks like. My gut says you may need to change your cap table some, perhaps buy out some and add some new investors, to get everyone aligned. But that is knowing only what you said above. Depending on the the sector I could give other suggestions.
commentor profile
+12 more replies.
Join the discussion