2022-01-21
How lucky I am to have something that makes saying goodbye so hard.
— A.A. Milne
Square was my dream job. I never thought I'd be good enough to work there. But through a series of fortunate events and people taking bets on me, I joined in late 2016 to help start the Restaurants team [1]. There were a few engineers, designers, and me (the product manager). The company was about 2,000 people. The New York office was just over 100. All the product managers (almost) fit in a single conference room. Fast forward and I lead an organization of 100 across product, engineering, and operations. The company is approaching 10,000 strong. And we have expanded into five different businesses.
It's time for me to go back to square one.
I joined Square for three reasons. First, I wanted to see how fast I could move in a larger company. I only knew startups before Square and wanted to test the next order of magnitude in size. Second, I wanted to experience what I called “full stack design”. We all know full stack engineering, but the same concept applies to design. There are few companies who understand the connection between brand, marketing design, and product design — all way down to the colors and fonts we choose. Square was (and is) one of the few that qualifies. Third, I wanted my work to mean something. Square stood for economic empowerment. Little did I know how deeply this would impact me over the years. To quote Nick Dimichino, "Small businesses are perfect".
It's time for me to go back to square one.
Square gave me more than I could have ever imagined. I made friendships that will outlast my career. I was given opportunity beyond any reasonable expectation [2]. I saw what led to great products. I fell in love with our customers [3]. I'll never be the same, and for that I am forever grateful. My time at Square was magical.
It's time for me to go back to square one.
Deciding to move on from something you love is never easy. When I finally made the decision, it took a lot longer than expected to truly understand what I wanted to do next. Yet once again due to a series of fortunate events and people taking bets on me, I found my next adventure.
It's time for me to go back to square one.
[1] Thank you to Bruce Bell, Logan Johnson, Matthew O'Connor, Mikael Westman, Brian Stegall, and Brad Seiler for taking a chance on me.
[2] I started as an IC product manager. Two years later, I started managing my first product manager but quickly shifted into a cross-functional leadership role (without any qualification, just the belief of my manager). More teams were shifted into my scope every quarter. I had no idea why. I just kept an open mind and held on for dear life.
[3] My favorite part of working at Square was interacting with customers. I would pay to do it. In fact, I do! Every time I get coffee, eat at a restaurant, or get a haircut, I look at what point of sale they are using. I ask what they think. I ask what keeps them up at night. And I think of how I could help them. Regardless of where I work, I don't think I'll ever stop. My wife hates me for it (it's terribly embarrassing). But I love it.