Lessons from Organizing Company-wide Hackathons

When I joined DigitalOcean in October 2016 as Chief of Staff to our CTO, one of my first tasks was to organize a company-wide Hackathon. I was intrigued as to why our leadership was so excited about a Hackathon; in my mind, it was an event for employees to work together and collaborate similar to a DO basketball game or dinner outing. Why were they so interested in the company-wide participation?

I did not get my answer until after the Hackathon. I realized not only were there positive outcomes around collaboration and team-building, but the actual outputs were extremely innovative, intelligent, and productive. As our VP of Engineering Greg Warden put it, “I love seeing the passion and ideas from people I don’t always interact with. The best ideas come from the most curious of places.” Enough said!

Over the past year, we’ve successfully hosted three Hackathons. From our initial Hackathon of 120 participants, we’ve successfully increased our participation to over 40% of our 380+ employee company. In order to achieve this growth, we constantly iterated each event. We’ve added guest technical judges to help evaluate the more complicated projects, extended the pitching time from 120 seconds to 5 minutes, and brought in fun extras like a barista, late night pizza, and happy hour. To foster a healthy sense of friendly competition, we give awards in categories like “Best Business Solution”, “Best Technology”, “Most Cross-functional Team”, and “People’s Choice”. All of our Hackathon participants get fun swag, too!

One of the best parts of the Hackathon is seeing projects that end up becoming a part of our internal toolset. Some notable past winners include:

• Porthole, a design-centric search engine for our Control Panel, which will be considered for our future roadmap.
• Food Ratings, an app that allows users to quickly rate the day’s lunch (we offer catered lunches to employees in our NYC HQ and Cambridge, MA offices). You can rate either the specific meal you just ate (i.e. falafel, or a rice dish) and/or amount of protein available:

• Plankton, a complex project that demonstrated how a large number of tiny Droplets (“plankton”) could be used to divide and conquer a large task. The plankton were designed to be as small and lightweight as possible, making it easy to spin up hundreds or thousands of them at a time. See the benefits below:

Many projects, including those mentioned above, focus not only on customer-facing tools, but they also optimize the employee experience. It was a unique balance, whereas some people focused on how they could improve their everyday life, while others looked to cloud computing.

Here are five tips to consider for hosting a successful Hackathon.

1. Leadership support. Our CEO Ben Uretsky constantly sends company-wide emails weeks before the actual Hackathons to express his excitement and support. He encourages all employees to participate, and encourages managers to support team participation by setting aside time specifically for the Hackathon.
2. Cross-functional participation. The teams that have created truly innovative products and addressed real, practical problems are cross-functional teams with members from all across the company. We put procedures in place to assure that both technical and non-technical people participate. Since Hackathons are technical in nature, it should be of the utmost importance to encourage non-technical colleagues to join teams. Their skills are desperately needed. Because our workforce is 50% remote, this also added another complexity. How can we make it feel like one, centralized Hackathon all over the world? We encourage remote teams to all meet at one central location, even if it’s not our office in NYC. If that was not practical, we encouraged teams to hack via Google Hangout. Pitches are also live streamed so everyone can participate (and even pitch) to our remote employees.
3. A work embargo. There are actually two parts to this point: 1) Make sure you get approval for a company-wide work embargo and get manager buy-in, and 2) Confirm you communicate that bottoms-up and top-down. When people are busy with work, teams are discouraged, lop-sided and usually s-t-r-e-s-s-e-d. To truly have focused teams, you need to cut out the noise (the noise being your routine daily responsibilities).
4. No limitations on project ideas. If your Hackathon’s true mission is to support innovation within your company, the best rule is to have no (or very few) rules around projects. Allow your employees to work on whatever they want, whatever problem they have witnessed, or pain point that needs addressing. The only rules we had were to disallow leadership from participating (because they were judges and resources), and for projects to be somehow relevant to DO.
5. Fun! Some Hackathons can still feel like work, and at some points, can be even more challenging (I only have 48 hours to make a super impressive product? Ugh!). But adding fun events, food vendors, and breaks makes it more enjoyable. At DO, we hired a barista to make delicious artisanal coffees, and we had pizza parties, and donut breaks.

Company-wide Hackathons are a great way to promote company cohesion in a fun and relaxed atmosphere. They give people room to be creative and to work with people across teams that they would normally not interface with in their day-to-day life. By giving people the space to experiment, tinker, and get to know each other, you give them permission to create something of value to themselves and even the company at large.

A scene from our most recent Hackathon this past October.

Jackie De La Rosa is a Senior Program Manager at DigitalOcean and focuses on overall strategy, business operations and executive initiatives. She was one of the first employees at DigitalOcean’s second office in Cambridge, Massachusetts.