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How to Pull Off a Successful Hackathon: Tips from the Virgil Truman Fall Classic


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    Hackathon, Broken Windows, Improvement Days, Developer Days. Regardless of what you call it, these collaborative events are a great way to foster higher levels of team engagement, morale and camaraderie – all necessary components to build a great engineering culture. We pulled off our first hackathon at Virtru in December after many weeks of planning and organizing. Scheduled in conjunction with our quarterly all-hands, our hackathon gave engineers the freedom to take a break from their regular commits to work on new projects that may advance our product, improve engineering processes, or explore a new tech that could be groundbreaking.

    Having successfully organized hackathons in the past, I applied these lessons learned when planning Virtru’s first hackathon. My approach revolves around the notion of ‘directed innovation’, meaning there should be a theme, purpose, or goal. Without some constraints, you may find yourself with a ‘not hotdog’ app and lots of time and resources wasted. That said, a directed innovation approach must also avoid mandating too many requirements otherwise it defeats the purpose of free thinking and innovative ideas.

    Hackathons provide members of the team the opportunity to highlight different expertise, gain leadership skills, and work under tight deadlines collaborating in ways outside of their normal routines. It’s a great way to professionally expand into new areas and show initiative. It also takes a lot of work to actually reap these benefits, but it is worth it. Let’s take a look at some of the core components that go into organizing a successful hackathon and how we customized it at Virtru. As you’ll see, hackathons are a great way to further develop your engineering culture, provide visible ROI for the C-suite, and build shared experiences across the company.

    Back to Basics

    When I joined Virtru last summer, I identified getting a hackathon off the ground as one of my first initiatives. Thanks to a large team effort and support from rest of the company –  including the C-Suite – we successfully pulled off our first hackathon with great fanfare. It takes a lot of planning and thought process to pull together an event like this and thanks to a team of volunteers at Virtru we planned and then successfully executed the Virgil Truman Fall Classic – Virtru’s inaugural hackathon.

    Think of it as planning a wedding where everything should be choreographed and orchestrated while allowing people to have fun. We had to create different working committees to take care of travel logistics, day of the event planning, securing office space, communication, judging, awards, food, and assisting engineers on the day of the event.  And just like a wedding, you need to stay within a working budget. This is another reason why an executive sponsor is so essential. Not only do they provide the top cover to ensure success and collaboration across the various departments, but it also helps maximize participation and demonstrate the corporate commitment to building an innovative culture.

    The prep planning is necessary, but an equal amount of time should be devoted to the actual guidelines and objectives of the hackathon to ensure its success. A hackathon is a cultural event and as such the name of the event, the rules, categories, evaluation process, and even mascot or swag all must be well-defined prior to the event. From start to finish, the organizer and identified committee members must commit to roughly three months of planning. While that may seem excessive, this pre-planning is essential to truly maximize participation, gain cross-departmental support, and build the excitement that drives the desired innovative outcomes.

    Introducing the Virgil Truman Fall Classic

    Virtru’s first hackathon was called the Virgil Truman Fall Classic, named after a mythical character, Virgil Truman, created by our CTO. Virgil Truman has evolved to represent our mission focused on making encryption accessible for everyone. It has to be so easy Virgil Truman can do it!  

    The teams were allotted 24 hours for actual coding, which meant the team selection happened prior to the start of the actual hackathon. There were several great ideas and horse trading began to solicit team members the night before the actual hackathon. That in itself was very exciting to see as engineers made passionate pleas to pitch their ideas and form a team. Since some remote colleagues could not make the event, we also live streamed the pitches, which had the added benefit of reaching a broader group of people across the company.

    Once teams were formed, everyone got to work. The energy and excitement on the morning of the hackathon was palpable. We allowed teams to work anywhere in the city. Some teams chose to whiteboard ideas and map out the UX while others dove straight into coding. It was great to see some teammates from Sales and Customer Service also get in the fray and try and get their ideas built out. Teams worked into the wee hours of the evening. A true measure of a good hackathon is that we should run out of beer, pizza and Red Bull, and that’s exactly what happened!

    Finally, it was time to share the results of their hard work during the final presentations. We chose a Shark Tank style format, with leaders across the C-suite as the judges, but also added a peer recognized award to ensure we covered all the bases. The final four categories were:

    1. People’s Choice
    2. Engineers Choice
    3. Customer Impact
    4. Innovative

    In addition to bragging rights, the winners received non-monetary awards with the team names forever etched on a plaque that hung in the halls of Virtru for years to come.

    There were several great ideas with a theme emerging around boosting engineering productivity, solving some key pain points, and leveraging TDF (new innovations in TDF that will be rolling out shortly) to build amazing encryption solutions.

    All winning ideas had the hallmark of a simple solution that solved a key pain point. Here are examples of some projects:

    • Running the entire SaaS locally
    • Implementing Geofencing for TDF
    • Containerizing current services
    • Implementing a ‘Secure Send from anywhere’ feature


    When a management team can’t trust engineers for a day to invest their time in intellectual pursuits it sends the message that the management team views engineers more like assembly line bots that churn out code day after day as opposed to the creative knowledge workers that drive technical innovation within a company. Of course, as with any creative idea it’s essential to provide some boundaries to make sure that teams get the desired result and it doesn’t turn into simply a ‘day of fun’ with no concrete outcome. With boundaries established, there are numerous benefits to the company, including new product features, process efficiencies, cross-team collaboration and connections, and maybe even a little press!  All in all, our first hackathon was a great success. We are already looking ahead and planning how to further improve so that each hackathon is better than the first.

    Editorial Team

    Editorial Team

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