[johngalt]

Sounds like you agree with everything I said until you edited my comment down to that sentence.

If there's honestly 40 hours a week of ops issues during the first hire/MVP/market fitting phase. One of two things is happening:

1. Your startup is so wildly successful out of the gate that operations/infrastructure needs to grow exponentially.

2. Your startup has produced something that is complete garbage.

Neither situation is likely, but I'll let you guess which scenario is more common.

A much more realistic scenario is that ops work starts off as 5hours/week and grows to 10, 20, 30, 40 etc.. over a couple years without anyone noticing. By that time you've got a team of 4-6 devs and operations issues have become an annoying interruption to all of them. This is where bad IT decisions happen.

[JonM]

On that point (needing a sys admin for say 10 hours a week), where should a currently devs only team be looking? Remote freelancer? Dev with ops / sys admin experience?

[johngalt]

Depends on the nature of the work. Begin with the understanding that operational concerns will never be zero hours. The best freelancer in the world will need guidance from the internal staff.

If you've already got something in place and operating at <10 hours a week, I'd keep it in house with whatever dev has more ops experience. Or whichever one drew the short straw after no one admits to having ops experience. You could hand it off to your newer hires to gain an understanding of what you do. The key is to define who responds to what.

Keep an engineer on retainer that you can call in to handle one-off builds and emergencies. Big changes/deployments where you can't afford to gain experience the hard way.