One Year Later

An engineer’s first year at Square

Written by Riley Strong.

In the year since I joined, many aspects of my life at Square have changed. Here are a few of my observations.


The most obvious change is our scale. When I started last April, Square was roughly 450 people. Now we are more than 800; and with our growth, previous structures and systems reached their limits. Physically, the number of our offices grew dramatically — now with a footprint in 6 cities globally. And in San Francisco, we moved to a new office with more than 150,000 sq ft and our own restaurant. Abstractly, many teams reorganized to accommodate new people and keep teams small. Our goal is to have no more than 8 people per team, which helps us move quickly and ensures everyone has a major impact.

Scaling our software to accommodate massive amounts of traffic, data, and engineers has precipitated change as well. From a development perspective, we had around 50 services when I started. We now have well over 200! Similar to the Unix philosophy, each service should do only one thing and do it well. From a development perspective, this means I can ignore a vast majority of the services and code at Square to narrow in on the task at hand — saving time and bugs.


Before Square, I worked at a startup with fewer than 10 people. There was little sense of code ownership, as much of the engineering was outsourced. Coming to Square was a breath of fresh air. My first few months were a whirlwind of learning new languages, frameworks, and patterns: Ruby, Rails, Ember + coffeescript, and proper TDD. All of these enabled me to help update Square Dashboard for our launch in Japan.

With each new product comes a new set of skills to master. Recently, I’ve been learning email templating, distributed systems, protos, multithreading, and some Java. These skills were necessary to build a service dedicated to sending digital receipts and launch Square Feedback. I love that not only do I get to ship exciting new products all the time, but that in order to do so, I am constantly stepping up my game and learning new skills.


There are some things that shouldn’t change, though. At Square, company culture has remained constant. We continue to ask tough questions to the team during our Friday all-hands (Town Square); we continue to spawn amazing products during Hack Week; and we continue to share notes from every meeting (even board meetings), with everyone to ensure transparency and ownership.

In one word, the culture at Square is thoughtful. I know people give each decision careful consideration. Every decision feels thoughtful chosen — from the furniture in our office, to company-wide priorities. That doesn’t mean I always agree or we get it right the first time, but it does mean I have enormous confidence in my co-workers to make decisions.

Change is a good thing. In the year since I started, Square substantially matured, onboarding thousands of new sellers, shipping tons of new products, and launching in a new country. But what keeps me coming back into work every day is not what changes, it’s what stays the same. It’s the thoughtfulness of (now) more than 800 people all working toward the same goal. I can’t wait to see what the next year holds! Riley Strong - Profile *Follow the latest activity of Riley Strong - Profile on Medium. 93 people are following Riley Strong - Profile to see…*

Table Of Contents