So we tried twice over 3 years with 2 different VP's. Both paid $300-400k and sourced through recruiters who charged $75k in recruiter fees. So we were getting what any VC would consider cream of the crop VP of Sales.
Yet both of them failed spectacularly. We went from closing business every month to (both times) sales stalling and flat lining.
The 2 VP's were smart people and they had seen success at prior companies similar to ours in size and scale and maturity (and deal size, sales cycle length, B2B, etc). So what was the problem?
Simply put, what worked at their prior companies didn't work at our company. And both of the VP's wanted to push us the founders as far away from the sales group as possible so the VP's could retain full autonomy with their team. Onboarding both VP's was a miserable experience because, both times, they clearly weren't interested in internalizing the hundreds of failed lessons (and success stories) that had gotten us to this point. So after a while we saw the whole sales team slide back into old behaviors and tactics that we as founders knew didn't work (because we'd already learned those lessons).
By the time founders get to the point of bringing in outside management, they've probably been running the company for many years. The fatal problem is when founders bring in outside managers who don't bother to understand the tactics the founders used to get the company to the stage its at, and instead they come in wanting to replicate experiences they had a prior companies, because that's what's comfortable for them.
Unfortunately, on the flip side, promoting from within isn't a much better option, either. I've seen it happen multiple times where extremely high performing IC's are promoted into Lead or Manager roles, and the company 1) immediately loses a high performer because they're now focussed on managing people which is usually a totally different skillset than whatever made them a high performing IC, and 2) the manager fizzles out after 1-2 years because they aren't practiced at basic management tactics like delegation, quit, and go back to an IC position at another company.
It's incredibly difficult to convert an IC into a manager. And it's also incredibly challenging to (successfully) bring in a manager who wasn't first an IC at your company.
"Founder Mode" to me is figuring out how to scale your company in a way that doesn't lose the "magic sauce" that got the team to where it is. "Magic sauce" being culture, processes, systems, tactics, lessons, knowledge, etc that founders used to get the company to where it is before needing managers to scale people.
"Founder led sales" ... "Founder led engineering" ... "Founder led marketing" are all dirty words when talking to VC's, PE, potential acquirers, because anything "Founder-led" isn't scalable and relies on the founder working at the company to work. Maybe "Founder mode" is a stage of a company where the focus is figuring out how to scale "Founder led X" beyond what has historically been seen as practical.
