What We Learnt Running our First Virtual Hackathon

Sidetrade Tech Hub
5 min readOct 12, 2020

By James Vickery, Jamie Hennerley and Yassine Fastani

SideHack2020 T-Shirt, Stickers and Pizza

A hackathon aims to produce exciting and valuable projects while providing an opportunity for teams from different countries to build new work relationships.

After eleven hackathons, which typically consisted of our entire R&D flying out to Paris, our twelfth was a challenge. Previous hackathons set the bar high, in terms of both productivity and fun. This year, we had a lot to live up to, and the COVID crisis to contend with as well!

Originally, the twelfth Sidetrade hackathon was to take place in the brand-new Birmingham Tech Hub in early April. A lot of planning effort went into this, including travel and accommodation, which had to be priced. As the hackathon edged nearer, it became clear we could not proceed as planned due to the pandemic. This was a real blow, and the hopes of our yearly hackathon looked to be low. A few months passed and Mark Sheldon, our CTO, came up with the idea of hosting the hackathon virtually.

SideHack2020: Our First Virtual Hackathon

The challenge introduced was running another awesome hackathon, but virtually — COVID made remote working a requirement and we had to adapt to this new way of working while maintaining the value of our past hackathons. The pivot to remote also completely changed the logistical side of planning, for example sending t-shirts rather than buying plane tickets.

Benefits of Running a Hackathon

For Participants

The purpose of a hackathon is to give each attendee a chance to break off from routine work, develop new work relationships, improve skills, and challenge themselves in new avenues — many Sidetraders have great ideas, and a hackathon is the perfect opportunity to develop these ideas into future projects.

For the Company

At Sidetrade, we always search for new ideas and ways to enable the team to innovate around their talents. Sharing knowledge, creating solutions to problems, challenging ourselves — this is our oxygen. A hackathon provides an environment that promotes these principles, free from distractions.

What We Learnt

Our first mistake was forgetting that the hackathon was in the calendar until a month beforehand! With the current state of the world, it can be difficult to keep track of time, or even know what month it is! Kicking off just a month in advance actually gave us just enough time, but logistics would have been more manageable if we had started sooner.

At Sidetrade, hackathons are not just about creative thinking, but about bringing staff together. Physical distance meant togetherness was trickier, but with a little imagination, we were able to boost team spirit and keep things fun.


For example, we made video conferencing entertaining by using online games like scribble.io: a free multiplayer drawing and guessing game. Along with paid expenses for drinks and food, participants embraced these perks of the hackathon, which helped them feel part of a big event, not just stuck behind a screen at home.

During the hackathon, we encouraged participants to post highlights of the event on the company’s internal communications platform. Prizes were awarded for the posts with the most likes.

Thinking of running a virtual hackathon? Based on what we’ve learnt, here are six handy tips!


1. Set a schedule

It’s difficult to anticipate the logistical challenges. What helped us was writing a schedule, not just for the hackathon itself, but also for the organisational milestones leading up to the event. For example: gathering ideas, forming teams, and sending out goodies early enough to dodge shipping delays.

2. Select Projects

We try to make sure that selected hackathon topics are not already planned in the product roadmap — setting time away from the usual work enables participants to be creative and innovate new ideas. That said, projects should stay relevant to the company’s mission!

3. Build Teams

Decide on teams by allocating people to the pool of project ideas. It’s important to do this in advance, to give teams a chance to meet (virtually, of course) and plan ahead so they can hit the ground running.

4. Check Infrastructure

Make sure teams have the infrastructure they need (e.g. servers and databases) to prevent delays that can block them during the hackathon. Company-specific infra, such as the VPN, should be prepared to handle the increased load. Being able to count on the infrastructure frees up people to focus on creativity.

5. Run Demos

At SideHack2020, we had fifteen teams, and two hours for everyone to demo: this divides into eight minutes per team. Allowing two minutes between each presentation for switchover gives each team six minutes to present. This is short, but has the advantage of forcing teams to be concise. This makes demos fast-paced and exciting! We noticed, however, that pretty much every team underestimated the time their demo would take. It’s best to have a moderator remind teams if they’re running out of time.

6. Foster social interaction

Don’t forget that hackathons are for team-building and networking. Since we could not physically get together, we relied more on our online company social network. Creative challenges such as getting people to post photos showing the event’s stickers and t-shirts drove engagement, kept teams up to date with each other, and built a sense of community.


Thank you for reading — we hope this article inspired you to run your own virtual hackathon. Why not share how your event goes!

Massive thanks to Hugh Wells for handling distribution to UK and FR, and to STKRS & Red Oak Roller for handling stickers and t-shirt printing with a tight deadline 💙🧡



Sidetrade Tech Hub

Views from the software developers, data scientists and other tech experts at Sidetrade — the global AI-powered Order-To-Cash platform: www.sidetrade.com