The middle market (and especially the lower middle market) is the most underserved segment in executive search. Almost nobody says it out loud, but I have watched the same pattern repeat for over a decade now. From recruiting management consultants into industry to building leadership teams in companies of all sizes ($20M to $10B, the first portfolio company in search fund to a mega cap case study), I have seen the problem, and it is structural.
Most search firms build their processes, staffing models, and engagement structures around a certain scale and complexity of mandate. That calibration works at the upper end of the market, where client teams are larger, search timelines are longer, and the process can absorb some inefficiency without it showing. It does not flex down cleanly to a sub-$100M revenue business.
Apply that same playbook to a middle market portfolio company and something breaks. The process is too rigid, too slow, and often staffed by someone still building out their own experience. The playbook does not get lighter for a smaller company. It just gets applied with less attention from the senior search professional who won that mandate.
On the other hand, a lot of lower middle market hiring gets handled by contingency recruiters. Contingency work is optimized for speed and volume, not diagnostic depth. Nobody gets paid to slow down and question whether the job description is 100% right, because the incentive is to fill the seat and move to the next one, often in a competitive non-exclusive environment.
That can work fine for a lower level, standard operating role. It does not work for a leadership hire inside a company that just took on institutional capital, has a compressed hold period, and is being asked to hit a specific value creation thesis. Speed without diagnosis is how you end up with a technically qualified hire who is wrong for the actual mandate.
As a result, sponsors and portfolio company leadership in the middle market often choose between two flawed options: a process built for a different scale of company, or a process built for a different kind of role entirely. Neither one is built around what the middle market actually needs: someone who understands the mechanics of a value creation thesis, brings a level of excellence and expertise in talent acquisition, sits close enough to the search to stay personally accountable every single day, and treats a middle market search with the same rigor as one many times its size.
What actually separates a good outcome from a bad one here has nothing to do with logo size. It is whether the search itself was built around the thesis, or just around the title.
A large firm running its standard process for a $40M portfolio company is not running a bad process. It is running the wrong one: calibrated for a different kind of mandate than the one actually on the table. A contingency recruiter racing to a placement fee is not running a bad process either. It is optimized for a different outcome than the one the sponsor actually needs. Neither failure is really about size. Both are a calibration problem, and calibration problems do not fix themselves just because the firm doing the work gets smaller.
One bad leadership hire at this stage is more than a bad outcome. It is six months of lost execution before anyone admits it is not working, then a second search on a tighter timeline with a board that has already run out of patience. Often with similar results, because nobody fixed the calibration problem the first time either.
This segment has waited long enough for a model built specifically for it. Not a lighter version of someone else’s playbook, and not just a smaller firm running the same one. Its own, calibrated from the first conversation to the actual thesis a sponsor is underwriting. That is what I built Harper Dawn to be.