Ryan Caldbeck's site

I’ve been interviewing a lot lately: ~35 this week. The most frequent question I get is, “What do you look for in teammates?” Here’s my answer:

Traits: I look for five traits: Integrity, intelligence, work ethic, teamwork, and pride (more here). I have found those five traits are foundational for both a team that is incredible individually and will typically work exceptionally well together.

I care about trust, and specifically I care that my teammates are reliable, credible, and authentic (more here). You will build trust with me through authentic communication and talking about your genuine bugs and features (like here).

Experience: I look for people who have achieved something extraordinary, in any form. Maybe you won a national championship in baton twirling or worked your way into Stripe from a small town and rose through the ranks to win a company wide award. People who have done something exceptional know how to repeat that level of performance. The opposite of that is someone that went to a fancy high school, a mediocre college and a third tier investment bank. That trajectory is as clear as the first.

If I’m looking at someone’s background I look for those who have experience at both world-class technology companies and startups. Experience at top companies shows you understand great engineering culture, and startup experience tells me you’re ready for the rollercoaster with resilience and excitement.

Mindset: I want teammates that have a growth mindset. If you’re an engineer I’ll ask you about your use of Cursor and similar tools because I want us to leverage the latest technology in both what we build and how we build. This also shows me your curiosity and your commitment to improving your craft.

Location: I’ve tried in-person, remote, and hybrid setups, and I believe startups work best in person. While I’m confident in what we’re building, I know some of our assumptions are wrong—we just don’t know which ones. In-person collaboration makes pivots faster and more successful, as it fosters the real-time communication and trust needed to adapt. The authenticity of a walk to lunch can’t be replaced by Zoom icebreakers.

Passion: I will ask you what you’re passionate about. I care that I understand someone’s passion and that they understand it. That can be Star Wars, education, or cancer research. If a candidate doesn’t have a clear, identifiable passion, I find they are unlikely to know what will drive them in the future. Their longevity tends to be short.