Photo: Chris Siebel

My eight-month Shopify sprint

How a small team made a big impact on my life and career

Chris Bolton
Dec 20, 2018 · 5 min read

I had some pretty lofty ideas about what I’d be working on when I started my second internship at Shopify. Now, as my tenure here winds down, it’s time to reflect on what turned out to be an eight-month long sprint.

For the majority of my time, I worked on what was jokingly considered a minimalist product team of just four people. Actually, we started with just three: a frontend developer (that’s me!), a backend developer (Jess), and a designer (Meg). It wasn’t too long before we realized that content strategy (Tamsin) was a critical piece of the product and quickly added her to our squad.

Our small size meant that we had to double up on many roles (Jess took on championing the project, Meg took product management and Tamsin and I filled in all the weird gaps in between). But less really was more, and our small size became a huge advantage after we figured out each other’s working styles. Our defined roles melted away as Jess took on the project roadmap, I made sure our tasks were triaged and assigned, and Meg managed our stakeholders. On a larger team, this would have been chaos, but on ours, it meant we could make faster and smarter moves.

When it came to making decisions, everyone showed up with opinions. There was only four of us so we could afford to debate each other (at least for a defined period of time). At the end of our debates, we would defer to the person with the most context. These instances of strong opinions, weakly held were great examples of Shopify values being used in practice.

Together, we worked on an app to support Hack Days, an internal two-day hackathon that Shopify hosts to do all of the things hackathons are good at: causing a bit of disruption, getting people to meet and work with new coworkers, and coming up with really cool ideas that don’t fall onto our existing roadmap. Hack Days also tries to minimize the negative things hackathons can bring, like being exclusive to developers and forcing terrible sleep deprivation.

The basis of the app was that it provided Shopifolk with the ability to create and promote projects before the Hack Days, and recruit others to join their project based on the skills required to make the project a reality. Then, during the event, teams could pitch their projects and other employees could vote in the app on their favourites. There was an existing tool to do this, but it hadn’t seen major development in four years. The Culture team approached us to build a new tool that captured the energy and spirit of Hack Days, while making it dead simple to use.

Working on a product in this context meant spending a lot of time with the Culture team to fine tune how the experience would exactly capture the “energy and spirit” of Hack Days. “Energy and spirit” are hard to write into a GitHub issue.

We also had to balance this with the fact that we had just under five months to build the app. Ruthlessness became our favourite word in sprint planning. If we were going to get the experience we wanted, we needed to be ruthless about which user flows we prioritized. Creating projects? Top of the list. Finding old projects from past Hack Days? Let’s build it, but keep it unpolished and spend the time saved on something more critical.

This conflict — between building something functional and building something that aligned with the event’s excitement — became most apparent when we were considering creating a splash screen for the app. The splash screen would have a fun 3D canvas with axes floating around the screen (on brand with “Hack” Days). The number of axes would be representative of the number projects created, so as the event approached the screen became completely cluttered with these random flying axes.

Was this functional? No. Could we save time by skipping it? Sure. Were other screens more important for user actions? Definitely. Did we build it? You bet.

This splash screen brought the much-needed energy and spirit to the app. It animated the magnitude of the event. Watching the number of axes fill up the screen over the weeks leading up to the event as more people created projects was actually exciting. It was what made this not just a product, but a culture product.

A screen cap of Sydney (Culture Designer) and myself hosting Hack Days 23

On December 6th, Hack Days 23 kicked off in Shopify offices around the world. The app came in on time (thanks to Jess’s realistic roadmap), well polished (Meg nailed the design), and easy to use (Tamsin’s copy brought an expert-level of clarity).

Moreover, the app helped to improve the event’s engagement within the company and paves the way for future programming-related changes in the future. There are lots of ways that Hack Days can evolve, and now it has a stable product foundation to do so.

One of the best parts of this experience was the ability to contribute to the product at every stage. From researching in the summer, to building in the fall, to actually running and hosting the Hack Days event in the winter, it’s been quite the journey. This sort of integrated product ideation, development, and execution has been one of the most challenging and rewarding experiences for me.

These eight months gave me the opportunity to take complete ownership over a product and its success. I realize this is rare for an internship and I’m forever grateful for it. But I also realize that it was really, really hard. Along with Hack Days, there were a handful of other projects and initiatives I became deeply involved in. “Deeply involved” became the slogan for my eight months — an accomplishment I am incredibly proud of. But “deeply involved” takes a lot of energy and commitment and I’m really happy to be taking some time now to breathe. As of Friday, this Shopify sprint will be over.

Good question. I actually don’t know yet. I’m headed back to school for another term, and actively exploring my options for next summer. There are lots of awesome things to work on at Shopify, although it may also be time to gain experience at another company (at least for an internship 😉). If you have any ideas, let me know!


Follow me on Twitter @cboltt and on cbolton.net
Big thanks to Tamsin, Daphne, and Jenny for reviewing and editing this post.