The Manager's Path

Introduction

In 2011, I joined a small startup called Rent the Runway. It was a radical departure for me to go from working on large distributed systems at a big company to working with a tiny engineering team with a focus on delivering a great customer experience. I did it because I thought the business was brilliant, and I wanted a chance to lead. I believed that with a little luck and some hard work, I could get that leadership experience that I was so eager to have.

I had no idea what I was getting myself into. I joined Rent the Runway as a manager without a team, a director of engineering in name and something closer to a tech lead in practice. As is often the case with startup life, I was hired to make big things happen, and had to figure out myself what that might look like.

Over the next four years, my role grew from managing a small team to running all of engineering as CTO. As the organization scaled, so did I. I had mentors, coaches, and friends who provided valuable advice, but no one was there to tell me specifically what to do. There was no safety net, and the learning curve was brutal.

When I left the company, I found myself bursting with advice. I also wanted a creative outlet, so I decided to participate in “National Novel Writing Month,” which is a challenge to write 50,000 words in 30 days. I attempted to write down everything I had learned over the past four years, everything I had personally experienced and several observations I’d made watching others succeed ...