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Making your first startup ops hire – what founders should look for

Sep 15, 2023

Most founders I talk to approach their first ops hire in a totally sensible but wrong way. Their typical approach is to look at the long list of admin debt they have accumulated, cry a bit, and then look for someone who has done those tasks before, plus a bit extra. However, the reality is that attributes >>> technical expertise when it comes to your first ops hire.

This person will have a disproportionate impact on your company culture. They'll do work that affects everyone on the team personally, and hopefully ensure the founders can focus on finding product-market fit and making the company a success.

With that in mind, these are the top three attributes they need...

Attribute 1: Extreme optimism

Anyone on the team at any level of seniority has to be able to ask your ops hire for help without worrying they're going to be annoyed. No request should feel too trivial. Additionally, most founders work directly with the first ops hire, so it has to be someone they want to talk to multiple times a week, even if it's about boring ops stuff (that we ops people love).

Your ops hire has to believe that all problems are fixable. This still means taking problems seriously, but (and I know this sounds cheesy) you want your ops hire to relish the opportunity to put out fires and make the lives of the team better as a result.

Antipattern Someone who sighs, rolls their eyes, or panics when hit with an annoying problem.

How to interview for this

  • Tell me about a time you got something done in a stressful situation when everyone else was panicking.
  • What is a process that you implemented which was important but boring for your team to follow? How did you get them to engage?

Attribute 2: Willingness to eat a lot of shit

Ops is a 100% defensive position in the early stages. Many people think it is about building structures and systems for hyper scale, but the reality is that up to ~50 people you are just putting out fires and making sure no one gets arrested. This means an ops person is only fixing problems, often problems they should have anticipated.

Working on many small things means more opportunity to make mistakes, many of which affect people personally, e.g. payroll, benefits, expenses. Team members will then (understandably) get annoyed, and your ops hire has to be totally unflappable. On top of that, team members will ignore the ops person's emails/messages/policies and then get annoyed when something doesn't work.

In both situations, your ops person needs to deploy their sunniest demeanor and gratefully fix the problem. Not doing so is the equivalent of telling off your users for complaining about your product.

Antipattern Someone who considers certain 'boring admin tasks' to be beneath them.

How to interview for this

  • Tell me about a time that you were blamed for a mistake that you felt was someone else's fault? How did you respond to it?
  • What is the biggest disappointment you have had in your career to date?
  • What is the most ridiculously trivial thing you ever did to help your team out?

Attribute 3: Total dependability

Your first ops hire is going to have top-level admin access to everything – banking, passwords, AWS etc. If they don't, you're wasting your time – wait to hire someone you trust with this stuff.

In addition to trusting them with the information, you need to trust they'll be available. While you shouldn't expect your ops hire to work all evenings and weekends, having a wonderful work-life balance doesn't quite apply when you're hiring a single point of failure for a bunch of your systems.

It is reasonable to expect your first ops hire to occasionally jump online out of hours to give someone access to an account, answer an urgent legal question, or look into a suspicious bank transaction. And, per Attribute 1, they should make it easy for you to ask them.

Finally, your first ops hire needs to recuse themselves from general office gossip, irrespective of seniority. If they are doing payroll for example, you need to be 100% confident they're not sharing this stuff with the wider team.

Antipattern Someone who is literally never available outside of the 9-5

How to interview for this

  • You'll generally pick up on this in the interview when you see how they talk about their previous places they've worked.
  • This is probably something you also need to validate through references (when available).

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