I like the writeup, but I wonder what size your startup has to be before this kicks in. Under N engineers, isn't the CTO just the founder with the most technical experience?
The "five essential skills" are critical on day -1 of the start-up. If you select the wrong platform, aren't aware of what it can do, can't come up with many options to do each of the things that need to be done, don't find the right 80/20 compromise, and can't recruit more technical talent, your technology start-up is screwed from the get-go. It might burn on for a while, but it'll all turn to ashes if you don't have a good start-up CTO.
Yes, absolutely. We didn't even formalize titles until we were in the 10-20 people range. I served as both CTO and VP Eng until the company was about 65 people, and it was starting to strain but was not a total disaster.
