A Hackathon to Honor a Legacy

Today we’re turning the blog over to Sean Kelly, Senior Engineering Manager, CBI (Core Business Infrastructure) and one of the organizers of this year’s hackathon. Sean has been at Klaviyo for a year and is based in Boston.

Last month, Klaviyo ran our second-ever hackathon. I volunteered to help organize and MC it and want to share how we made it happen. I’ll walk through the planning and judging, share a bunch of photos, and even tell you the name of the winning team.

(Regarding the details of what was hacked…we had 31 amazing teams. You may see some of their ideas coming to a Klaviyo product release near you…but you’ll have to wait until then to find out, as the hackathon ideas were so inspiring that we decided to keep them under lock and key until they’re ready for our customers!)

I’ll start with the name and logo. Klaviyo was recently devastated by the unfortunate passing of our long-time friend, coworker, and partner in crime Ben Liang. Ben was a tentpole of our culture and product direction, as well as a builder, a hacker, an entrepreneur, and a mentor to many of us (with an impeccable sense of humor, to boot). Because of his impact, we felt it was only fitting to name our hackathon after the man himself, and honor his legacy in a way that he would have approved of. Going forward, all Klaviyo hackathons will run under the banner of his name and his incredible spirit.

We miss you every day, Ben.

If you’re wondering, that’s an artist’s rendering of one of Ben’s beloved birds.

One of the hard parts of a hackathon for many would-be participants is coming up with an idea, or finding other people with an idea exciting enough to want to spend a few days hacking with them. To help combat this and get as many people hacking as possible, we created a pitch board, where anyone in the company with an idea could post about it and seek assistance. Additionally, anyone without an idea could take a gander and find something that made them think, “Hey… why haven’t we built that yet?” and get inspired to join.

To begin, we asked people to fill in the pitch board async. Then we ran a matchmaking session, where folks with ideas could pitch them, and folks in need of an idea could be wooed to join existing teams — or to form new ones entirely. It worked! Right after, we saw a big uptick in newly registered teams and additions to existing ones.

We settled on the week of March 20th for the actual hackathon as a nice send off for our first quarter. It was on teams to coordinate and ensure they were ready to hit the ground hacking come that week. Many folks traveled into Boston to participate, but we still had a good number of people hacking remotely, showcasing the strength of our hybrid approach to work. Depending on travel arrangements and team readiness, teams had Monday through Wednesday to get their hacking in, with the final judging taking place Thursday in a whirlwind of presentations and demos.

But before we can talk about who won, let’s talk about how they won.

The judging process was crucial to get right, and so we spent time coming up with three key categories, and one tie-breaker category. These were creativity, thoroughness, and impact, with the pitch itself as the tiebreaker. This way, we judged teams not necessarily on their ability to pitch, but on the merits of the work. Where we needed to break a tie, then we’d talk about who put on the better show. This was the best way to honor the spirit of the hackathon and still encourage folks to put effort into their presentations — a great idea with a poor pitch could still lose to a great idea with a solid one!

You can see the strength of the “design by committee” approach with how we named that second category!

To make it possible to complete all judging in one day, we randomly assigned each team to one of three rooms, each with its own panel of judges, all assessing according to the criteria above. These panels were made up of more senior members of the organization, as well as fellow engineering leaders, so that we got a holistic set of feedback across all the projects presented.

From each of the three rooms, we stack ranked the scores and selected the top two presentations. This helped us whittle down 31 ideas into six finalists. We allowed teams five minutes to present, and three minutes for judges to ask questions. We also baked in bathroom break time, an important part of any densely-packed schedule, and a free tip for any aspiring hackathon planners out there.

 

Collaboration was the name of the game during the week.

 

Our world class IT team, keeping the nerve center of Klaviyo running, while enjoying delicious Prospector Popcorn — one of thousands of food brands that use Klaviyo to grow.

 

Here we have the Hack Hubbers team, working diligently to wow the judges. We’re still trying to identify the green-sweatered individual to the side. Any leads are appreciated.

What’s a hackathon without food and swag? As you can see from our calendar below, we knew how important it was to pace ourselves when giving out high quality t-shirts and world-class snack offerings from our customers. We also made up fantastic stickers and brought in catered lunches from local Klaviyo favorites, ensuring our folks were well fed and well dressed throughout the week.

Our CTO Allen and VP of Product Jen distributing snacks and drinks.

 

Our agenda for the week, complete with swag, snacks, and judging.

 

Some of the amazing swag we came up with to celebrate the hackathon, held up by yours truly.

For our final round of judging, we brought in Klaviyo’s two co-founders — CEO Andrew Bialecki and CPO Ed Hallen, alongside our CTO Allen Chaves, our VP of Product Jen Kessler, and our VP of Design Pree Kolari. Our six finalists presented in our atrium and the judges had an extra two minutes to ask questions!

Finalists and audience members huddled together as they prepared for the final presentations.

 

Team Yamato III, named after favorite local eatery Yamato II. We did not receive any compensation for this promotion.

 

Immy and Will from team kMeasure giving their final presentation. Immy can be seen dual wielding microphones, which is a level 8 presentation skill.

 

Judges CTO Allen Chaves, VP of Design Pree Kolari, VP of Product Jen Kessler, and CEO Andrew Bialecki, who can barely believe what he’s seeing out of these hackathon teams! Judge Ed Hallen, not pictured, was dialed in remotely to round out our hybrid panel.

Without further delay, our winner…team NapkinGist!

CEO Andrew Bialecki with our grand prize winners Nick Vessella, Vinicius Aurichio, Ezra Freedman. Not pictured is final team member Nick Sypteras, who had a train to catch.

If you’ve been keeping your eyes on the recent moves Klaviyo has been making to support developers, you can guess where we’re headed with a team name like that…

Here are a few lessons for next time, or for other organizations running a hackathon.

Get super clear on not touching production — This should be obvious, but in the heat of hacking, it’s tempting to make use of production in creative ways. Also, for certain more data science-centric ideas, a team may need actual user data. We crafted strong guidance on what you could and couldn’t do, but there is always room for improvement. We’ll be taking feedback from teams and weaving that into future hackathon rules so that everyone is always clear on what is and isn’t acceptable.

Remind non-engineers to participate — We needed to emphasize over and over that non-engineers could form teams and partner with engineers to bring their ideas to life. From feedback, it’s clear that we needed to start that message even earlier.

Timing is critical — We worked backwards from the final judging process in order to understand how many teams we could support, how much time judging and presenting should take, and how the judging itself needed to be orchestrated so everyone had a good experience. Literally no one will be on time for their presentation slot even with a lot of careful nudging, and so plan to be getting the next two to three presenters ready while the current team is giving their pitch, to ensure a smooth transition between teams with minimal downtime. Also, timers. Buy timers and give them to your MCs!

Plan for change — Teams are going to drop out, re-form, or try to sneak in after the “official” deadline. Your CEO might call an audible and request some day-of changes to the final presentation schedule. Judges may mysteriously go missing throughout the day.

In a hackathon, anything can happen. Don’t get too married to your existing idea of how the day will work, and focus on making sure both the hackers and the audience get the best experience possible. It’s like a wedding — a lot of little things will go wrong, but only the organizers are going to notice it. Everyone else is gonna be too busy celebrating the presenters and cheering for the winners to notice the little things.

Understand your motivations — Here were ours:

1. Give our folks the space to try ideas, work together in new ways, and have fun building.
2. In keeping with #1, honor the legacy of our friend and pillar of our culture, Ben Liang.

We hoped we achieved the second by focusing on the first. We kept the spirit of Ben in mind during all of the planning. We know that Ben’s impact will be felt for years to come, not only in the work that he did on our software, but in the memory of who he was. Our hackathon will now be an ongoing tradition that reminds us of Ben and the culture he engendered.