But most of us under-hire at the senior level for one reason or another as we cross $1m-$2m in ARR, and there are two key times almost all founders hit organizational walls trying to do too much themselves:
Trying to be the VP of Multiple Functional Areas beyond the date you have to; and
Trying to manage all the functional areas beyond the date you have to.
Both sort of sneak up on you, and slow down your growth. The first wall you tend to hit is between $3m and $5m in ARR if you don’t have “all” the VPs: VPs of Sales, Marketing, Customer Success at a minimum, Product ideally, and often, Engineering. If you don’t, you just hit a scaling wall doing it all yourself. Each functional area needs a full-time VP to scale. There is just too much going on by this point, and the complexity begins to grow an order of magnitude. And you just don’t have the time. Sales slows down. Leads plateau. NPS drops. Releases slip. Customer visits decrease. You need a seasoned owner for each of these.
The next wall you hit tends to come up around $10m ARR or so. It’s when you finally have all the VPs, and you add a few more, and you’ve sort of figured it out, finally … and you have 8+ direct reports. This is just too many.