platform / 014

SideHack 2024: you are nothing without your team.

published
11/09/2025
author
Mark Sheldon
read
4 min
Hack team imagefig. 0 / platformrev 2025.09 / sidetrade r&d

CTO rule number one: you are nothing without your team. I have believed that for a long time, but every so often a week comes along that proves it beyond argument. SideHack 2024 was one of those weeks.

We have just spent five days together in Portugal at our annual hackathon. [Rob Harvey](https://www.linkedin.com/in/robharvey1/) and I came home convinced we have the best team in the world, and this post is an attempt to explain why, and to record what happened before the details blur.

01 / the week in numbers

What five days looks like

SideHack is not an evening with pizza and a leaderboard. It is a full working week where the whole engineering and product organisation gets on planes, forms teams, and builds things that were not on any roadmap. The rules are deliberately light: pick a problem you care about, find people who care about it too, and have something real to show by the final afternoon.

120+

Sidetraders in Portugal for the week, from every engineering and product team.

18

Projects delivered and demonstrated live on the final day.

5

Days, from first whiteboard to last presentation.

02 / what got built

AI everywhere

Every year the projects tell you what the team is thinking about, and this year the answer was unambiguous. AI was not a track or a theme. It was the default. Almost every one of the 18 projects used a model somewhere, and a good number of them used models to do work that a year ago we would have assumed needed a person.

Some of what was demonstrated is game-changing for our product and will show up in front of customers over the next twelve months. I am not going to spoil those here. What I can say is that the ideas came from the people closest to the code and the customers, not from a strategy document, which is exactly how it should work.

Product innovation
Prototypes that push the Order-to-Cash platform in directions we had talked about but never built.
Several are already being scoped into the roadmap.
Engineering tooling
Teams building for themselves: faster feedback loops, smarter automation, less friction shipping.
The unglamorous work that compounds.
Showstopping demos
Live presentations to the whole company, no slides-only entries allowed.
The bar for a hackathon demo at Sidetrade is now uncomfortably high.
fig. 1 — Eighteen projects, three rough buckets. The lines between them were blurrier than this suggests.
03 / why it works

The format is the point

People sometimes ask whether a week away from the roadmap is a cost we can afford. I think the question is backwards. The week pays for itself several times over, and not only in the projects that ship.

01
Self-forming teams

Nobody is assigned. People who have never worked together find each other around a problem, and those relationships survive long after the week ends.

02
Real constraints

Five days, a live demo, and an audience of 120 colleagues. Constraints force decisions, and decisions are where the learning is.

03
Permission to be wrong

Half the value of a hackathon is discovering which ideas do not survive contact with a prototype. That is cheap to learn in a week and expensive to learn in a quarter.

04
The whole company watching

When the demos land, everyone in the room understands what engineering is capable of. That changes conversations for the rest of the year.

04 / not just the work

Running, beaches and terrible karaoke

A hackathon that is only a hackathon misses most of the point. Being in the same place for five days meant morning runs and bike rides before the laptops opened, beach time in the afternoons, a Hawaiian night that will not be forgotten by anyone who has seen the photos, and a lot of late night dancing.

There was also karaoke. Some of it was terrible. All of it was worth it. Teams that have sung badly together in public tend to ship well together afterwards.

Hands down the best Hack we have run to date.
05 / what comes next

The next twelve months

I am excited for our customers and our investors, because a meaningful part of what they will see in the product over the coming year started life on a whiteboard in Portugal. I am more excited for the team, because they built it, and they know it.

If you read this and wanted to be in the room, we are hiring. Come and be part of SideHack 2025.

HiringWant to be part of the next SideHack? Sidetrade is hiring across engineering and product. Open roles at sidetrade.com/careers
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