A Square Retrospective

It’s been an amazing four years at Square.

By the time I write and edit and post this, it will be over a month since I’ve parted ways with the startup. Despite the time off, I haven’t made enough of a dent in my big list of “things to do with my time off”1, as it turns out other, more mundane things needed attention first anyway. That said, I’m still extremely appreciative of the time I’ve had away from work, and I’m thankful for having the means to spend more time on family and hobbies.

First Day at Work

I still remember my first impressions of Square. I had interviewed around April of 2011, and officially joined the team two months later. Back then, the company employed around 100 people, crammed into half a floor of space inside the second story of the historic SF Chronicle Building. Even back then, Square’s attention to detail shone through the office space: the work environment was tidy, the city-square-themed conference rooms were well-designed, and inforads permeated the entire space2.

I even remember attending the first Town Square, and sat dumbfounded from listening to the impassioned speech by co-founder Jim McKelvey on why we mattered. This was a company, driven by a strong mission, with a powerful blend of design and engineering and product management taking on an entrenched financial industry and making major splashes. It sounded and felt like that proverbial rocket ship, one whose ride was worth taking.

Square Dashboard

I’ve lost track of the number of teams I’ve been a part of during my stay, but my main achievement has been building the Square Dashboard3. The project started out as a simple enhancement to the existing website built to track deposits and transactions, but with the work of a really talented team, we rewrote the site and eventually scaled up the app to enhouse a dozen fully-fledged Square products.

Our team were one of a handful of major applications to bet on EmberJS, back when it had a different name and pushed out new, sometimes incompatible betas monthly. Looking back at that decision and the evolution of our code and processes, I’m happy we made the right call; we didn’t exactly plan it, but the scalability of code and embedded best practices has carried us much further than I would have imagined back with our initial launch.

All that time spent building the Dashboard has taught me a little about product resonance, especially with enterprise and business-centric software. The core design tenet of simplicity – which has become the de facto standard in customer-focused products – doesn’t fully apply to business products. In many cases, business users have needs which are complex and multivariate, where simplification no longer makes sense because there’s no way to unify options or automate disparate feature sets. There was never a simple answer, but each unhappy user provided an instructive lesson and an opportunity to iterate, provided we did not iterate too often; interface instability became acutely painful to our merchants at times.


Personally, I was fascinated by the company around me as it grew in size and scope and ambition and importance. There aren’t many companies that go through rapid expansion, and I was lucky enough to have a front-row seat as Square doubled, then doubled again every metric that mattered. That rush of spinning up new teams and offices, launching new products to overjoyed users, and perusing press coverage embodies the best startups have to offer.

Not that everything was great all the time. Our head of communications famously explained how press narratives work, and there had been multiple ups and downs through my tenure. When an organization adds an order of magnitude of people, the culture and communication patterns do evolve to manage that scale, and not everybody can or wants to evolve with the company as it continuously stretches itself. Some learn to cope with the differences and are able to grow themselves in conjunction, but others – not all that many, even though it always feels like a lot – chose otherwise.

What’s Next?

After some 4+ years of being a Square, it’s time for a change of scenery. The nice thing about being a software engineer in Silicon Valley is that job opportunities abound.

For me, that next opportunity will be Counsyl, a startup focused on genetic testing. I’ve always wanted to apply technology to healthcare and its related fields, and Counsyl has been doing just that to excellent results and impressive recognition. They have an top-notch product and team, and their recruiting process had gone way above and beyond my own expectations as a candidate. I’m excited to take all that I’ve learned from Square – its engineering and management and growth and product and design practices – and seeing how they apply or don’t apply to something as different as biotechnology.

  1. I had wanted to get better acquainted on ReactJS and Swift, for instance.

  2. This was well before every other startup in SF started rising tons of money and hiring famous architectural firms to help them build out their own offices.

  3. Fun fact: it took months of deliberations before we eventually decided to just keep the placeholder name.

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