How to interview with a startup CEO (by a startup CEO)

What do you look for when you interview startup sales/marketing/product management candidates?

I’ve found that in the best interviews with non-technical people I’m usually the one doing most of the talking.

For example, the best product managers asked lots of questions to help them understand:

  • what exactly we did
  • for whom
  • what we were good at
  • what we were struggling with

In other words, be prepared for your interview, ask a lot of questions, listen, and learn.

Then you have what you need to sell your unique fit with the startup and the specific role you’re targeting.

What’s a good way for someone who doesn’t have a software engineering background to learn about a highly technical product like Datadog before the interview?

A combination of two things:

  1. Using the non-technical employee’s most important weapon: listening carefully to what people have to say. That means asking your technical friends, reading-up on forums, and reaching out to startup investors if you know any.
  2. Rolling-up your sleeves and signing up for the product on your own. You may not understand everything you’ll see. Nonetheless, this shows that you’re not afraid to get into the details. And this will also give you more questions to ask during your interviews!

When and how are you most receptive to outreach from potential candidates?

There’s never a bad time to approach me about a job. As a CEO, I spend more than 50% of my time on recruiting, so it’s one of my top priorities.

Just know that whether you reach out via email or in person, being concise and to the point is key.