I'm the CEO of a service shop (developers). We currently have 20 employees. What are qualities that I should be looking at when hiring for an operations position to help me with day to day tasks? I'm also torn between hiring someone from the outside with experience, or promoting someone that I trust with less experience.
I would try to hire into your weakness and might take an inventory of exactly what you expect the candidate to aggressively deal with that will help your company scale. It seems probable that you are hiring your ops employee before an HR employee, and finance employee so if that is the case you will want to make sure the Ops candidate you select has the ability not only to just handle those roles but to also transition those responsibilities as the company grows. When I think of ops I think of day to day management but also strategy.
Promoting someone from within might be an easier and more comfortable route but an external candidate will most likely challenge you in the right sort of ways and compliment you in others, this uncomfortable chafing will lead you to be a better leader and strategist within your business. Good luck!