How to run a Hackathon during a global lockdown

We had our first Yieldstreet Hackathon at the end of June 2020 – right in the middle of the lockdown due to Covid-19 pandemic. It was a challenging but interesting experience and ultimately went very well. As of this writing, it’s been a few months since the Hackathon happened, and the passing of time gives an additional perspective. In this article, I wanted to share the lessons learned – hopefully it will be useful in your organization as well.

Why Hackathon?

There were three main reasons for conducting the Hackathon:

  • Encourage creativity and innovation – at Yieldstreet, creativity is built into our DNA – our company is built on exploring previously uncharted territory in the investment world. However, we constantly need to challenge ourselves to think differently and continue innovating, and Hackathon is an essential part of that process.
  • Improve cross-team collaboration – constantly working with the same people is great for productivity as you get to know your colleagues’ strengths and weaknesses, and build deep trust (which is the basis for high performing teams). But – with our team split across five countries and three continents, and especially with everyone working from home during the Covid-19 lockdown, it is even more important to foster new ways  for people to connect outside of the regular work routine. When forming Hackathon teams, we encouraged everyone to work with people they don’t usually collaborate with.
  • Increase the team’s morale during difficult times – 2020 has been a challenging year (and as of this writing, it’s not over yet). Back in June, Covid epidemic was raging, most people were unable to leave their home for three months, the economy wasn’t doing well, and there was much social and political turmoil in the US and the world. Taking care of our employees has become one of the most important focus areas for Yieldstreet, and the Hackathon was one of those efforts.

I don’t want to spoil the ending, but we have wildly succeeded on all of those counts.

Ideas and Teams

We started the Hackathon prep by having everyone pitch their ideas for projects. Everyone was eligible to submit Hackathon ideas – not just product, design or engineering – and they got two minutes during an all-company Zoom call to recruit others to work on theirs. We had no constraints – crazy ideas welcome! The only rule was that it needed to be related to our business. The ideas were divided into four categories:

  • Top of the Funnel & Making Deals
  • Investor Delight
  • Operational Excellence
  • Deciding with Data

After the idea pitch meeting, everyone added their names to the team they wanted to join and we were ready to get started.

Hacking Away

After the pitch meeting, we ended up with 12 teams. Each team got two full days to work on their projects. Yes, that means that the regular work was paused. While it may seem more “efficient” to run the Hackathon on nights and weekends (and some companies do), we firmly believe that the only way to make the experience enjoyable and worthwhile is to treat it like real work – which it is. It’s hard to come up with innovative ideas and turn them into projects when you’re expected to do it on your own time – especially in a lockdown during a global pandemic.

The biggest challenge Hackathon teams needed to overcome was remote collaboration. How do you meet with your team? How do you collaborate effectively? How do you show your teammate code that’s running on your local machine without deploying it somewhere?

Thankfully, with our engineering team split between the US, Brazil, Argentina and Malta, we had ample experience in working remotely:

  • Teams were in constant communication with each other, on Slack and Google Meet
  • Designs were created and shared for rapid feedback via Figma
  • To share code developed on local machines, we used OpenVPN – which everyone already had set up for access to our servers.

The Grand Finale

After two days of furious hacking, it was time to demo the finished projects, vote for winners and the award ceremony. Each team got six minutes to present (to keep things fair, the order was determined randomly). The entire company gathered for this meeting – which took place over Zoom – and everyone was blown away by how much were teams able to accomplish in just two days.

Everyone proceeded to vote for their favorite projects. The winners for each category were determined by a popular vote, and a special “Leadership Choice Award” was given to the project that didn’t win, but would have the biggest business impact if implemented.

The concluding act for the Hackathon was the Award Ceremony. We had a bit of fun organizing it like the Oscars – winners were announced by our executives who opened the sealed envelope and said “And the winning team is..” . Every winner was required to give a short acceptance speech. The prizes were also announced – every member of the winning teams got a cash prize and some exclusive swag. After the ceremony, we all stayed on the Zoom call for a bit longer, where a Hackathon discussion turned into a company-wide happy hour.

One of the prizes for the lucky winners

Takeaways

Looking back, it’s hard to overstate the Hackathon’s impact. Some really cool projects were implemented, with a few already in production. The Hackathon brought everyone on the team closer together, provided a much needed distraction and a morale boost, and spurred creativity and innovation throughout the organization.

From the beginning of the Covid-19 lockdown in March and throughout June, it was one piece of grim news after the other. And maybe that was a coincidence, but it seems like the Hackathon was the turning point when things started to slowly change for the better. We’ve decided to make the Hackathon a regular part of our Yieldstreet experience, and are planning the next one by the end of this year.

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