I am in the midst of writing a follow-up article to one I have written to address some myths about startups and operations executives. In 15 years I have been through 9 startups (co-founder in 2 and early employee in most). In almost every one them I held different levels of hands-on and operations leadership roles. Every single founder, who brought me onboard, had certain "catalyst event" that made them realize it was time to bring on someone with deep expertise in scaling companies.
So this question is for those founders, who did bring a COO, VP, or Director of Operations to help them manage and scale the company. When did you know it was time?
In my case companies I joined had:
P.S. I know on the coasts and in certain tech companies "operations" sometimes gets too narrow of definition (which should be DevOps), so to address that, I have an article "What do operations people do?"
There is a related post from Reid Hoffman (Greylock, Linkedin, Paypal) on if/why/how founders should hire an experienced CEO In this article, he references the 20 year practice of bringing in a "grayhair" to run things after the model is validated is starting to lose popularity. Also Ben Horowitz (Andreessen Horowitz) also late in 2012 made a similar point - why we prefer founding CEOs.
In my experience, I have found that there are large gaps between 1) validating the initial concept, 2) validating the business model, and then 3) scaling the validated business model. Many times skills needed to achieve one are not as important in another - and applying the same skills can lead to failure.
Mid step 2 / early 3 is where the COO/ Devops roles / responsibilities become more important: tech decisions in step 1 may need to be re-evaluated, as does operational costs, separation of duties, staffing. Some founders may be better suited / prefer to do operational tasks - others not. Others may not want to consider any other position than CEO. This is the dreaded founders dilemma that every startup founder faces (or is confronted with) - and requires personal introspection on how to approach it.