Building a Product Management Team from 1 to 2 Employees

Andy O'Dower

Head of Product, Programmable Voice at Twilio



When you are co-founder or CEO of a start-up company, you wear many hats and you are involved in all decisions. For instance, in one of my previous companies, I was the only person on Product. I would think strategically in the morning and tactically in the afternoon and night. Every part of the cycle was under my jurisdiction. But at some point, our timelines were getting slowed down because I couldn't keep up with being involved in every aspect and every decision of a growing product.

Actions taken

I decided it was time to hire one person to join me on the product team. Rarely does it make sense to hire multiple people at once at this stage. The first hire is pivotal; I've found that hiring your counterpart- someone who has strengths where you have weaknesses can be very successful. I thought about all the things I felt had gone well so far and all the things that I could have done better. Using this self evaluation, I looked for a potential hire who could fill in the gaps.

Lessons learned

In general, this process worked very well. However, I learned that in addition to finding someone with these skills, you have to find someone that you completely trust. It is hard to give up decision making when you have been used to doing all of it so finding someone you trust makes this process easier. You need to start slow and and build upon the things you delegate in order to create good delegation habits. Divide up work into what parts of the cycle you need to be involved in the decisions and in what parts of the cycle you don't (ex: strategy, roadmap, backlog, etc). If an employee makes a decision you don't agree with, you now have more information for what and how to delegate in the future. Use these data points. FInally, ensure upfront that it is very clear what areas need manager input and what are completely up to the employee; this will help you to stay on track.

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Andy O'Dower

Head of Product, Programmable Voice at Twilio

Leadership DevelopmentCommunicationDecision Making

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