sound advice, thanks a bunch. i just threw the executive titles out there since i think that's where they would ideally lead to, and i don't exactly know how to speak to the people we are looking for to help us. I will read the medium post you linked now! if you are ever in the bay area, hit me up, id love to meet for coffee.
Just to add to the general chorus, what you really want are good consultants (or coaches, depending on your vernacular) for the specific problems you're facing. Crossing your fingers and letting a new CTO or CEO figure out the big picture for you is attractive, sure, but the risks are too high.
After you've filled in the blanks, you'll feel much more comfortable, and at that point make some hires to deal with those specific business areas, while still maintaining overall control. As others have said, you guys are doing something right or you wouldn't be in this position in the first place.
If I was over in SF, I'd love to help you out, but I'm based in Sydney.
I think Paul's advice is sound... get consultants/coaches, but keep the leadership !!
I don't have a company myself, but some people I know who do have had a lot of success linking up with the local university's Business programs (MBAs, or in my case a Master's in Management of Technology)... many professors have consultancy businesses on the side, and you can also draw on the students' abilities - for example, as a student, I got assigned to a 2M/year company, they gave us insider access and, with the teachers' guidance, we gave them a free consultancy.
I also recommend a Master's in Management (MOT or an MBA), running a company yourself you'll get a lot of value out of it. I see many California universities offer one (MOT or similar), maybe there's a graduate here on Hacker News who can recommend one.
Going with the "get good consultants/coaches" - if the coaches/consultants are good, and a good fit, then see if you can bring them on board.
Traditional "interview and put in place" hiring strategies are built around the needs of traditional large organisations with massive amounts of existing organisational momentum and plenty of time to recover from mistakes or retrain duff hires.
Small fast-moving companies don't have those advantages, and shouldn't hire that way. You're obviously innovative - don't forget to apply that creativity to your business processes.
