Operations and marketing directors for intelligent transportation

Why CharterUp’s director searches were hard

CharterUp connects charter bus fleets with the customers who need them. After securing its Series A, the company had to scale leadership across Engineering, Operations, and go-to-market, all at director level and all at once.

Three director searches across three unrelated functions is not one search run three times. Each has a different candidate market, a different assessment, and a different set of people who can credibly interview for it. Run sequentially they take most of a year. Run in parallel by a team that has just raised and is already stretched, they compete for the same calendar, and the search that gets attention is whichever one the CEO asked about most recently.

Director level is also the hardest band to hire at this stage. The company needs someone senior enough to own a function outright and hands-on enough to still be doing the work, and it is interviewing them without the internal benchmark a bigger company would have. Get it wrong and the mistake is not visible for a year.

Why the engagement model mattered

Paying a traditional agency fee on each of those searches is a hard fit for a company that has just raised and is planning its headcount for the year, because the cost of the hiring program only resolves one offer at a time. The searches were bought instead as a pre-purchased plan with OutScout, agreed before the work started, so that cost was a known line from the outset.

The searches OutScout ran

A talent partner ran the director searches together rather than as separate engagements, carrying what one search learned about the market into the next. A Director of Operations and a Director of Marketing were placed inside two to three months, each from a tight set of matches rather than a broad pool, which is what let a leadership team in the middle of a post-raise build actually sit the interviews.

Why post-Series A director hiring is its own problem

The operators worth hiring at this stage have options and are usually mid-build somewhere else. They are not looking, and they will not run a slow process. The search comes down to identifying the short list of people who have done the job at this size, reaching them directly, and moving fast enough to finish before their attention goes back to the build they are already in.