Once a year we take our entire company on a retreat (it’s our 5th, and this year it was in Malta). It’s very expensive (costing ~£400k), but as a fully distributed company it’s has benefits. The purpose of the retreat is to fuel our winning culture by reminding everyone we’re winning (but haven’t won), and to excite people for what the next decade holds for us. It’s critical for us to retain the best staff, and the retreat is a way to give back, which I think contributes to employee retention. There were some unexpected learnings and reflections from this year, which I talk about later in this post.
Here was this years structure:
Mon - Welcome presentation focused on celebrating key company achievements. Such as hitting record high numbers, big clients landed, customer success stories, and key product/content launches!
Tue - In the morning we talk about vision and where the company is going over the next decade (why we exist, showcasing the impact of the company, how we’ll hit $100M ARR & reach 100M users). Followed by a fun afternoon of activities.
Wed (new) - We ran a hackathon for the entire day, where teams built products around company challenges. After a day of building and drinking a lot of RedBull we toured a Malta village and had dinner out.
Thu - This day is dedicated to teams, with department-specific workshops and social activities. The day (and retreat) concludes with an awards dinner, recognising standout staff members.
What I really like about the retreat is it gives me a chance to step back, reflect, and evaluate the company’s vision. Whilst the vision hasn’t changed (making the world more digitally secure), what we build, what we do, and what our brand means does. This year, and probably for the first time, I explained to the company how we go from 9 million users to 100 million, and from $45M to >$100M ARR. I believe its clearer now (in 2026) than its ever been, and presenting how we get there has helped a lot with my own clarity on planning, and aligning everyone in the company.
TryHackMe has no company calls (no all-hands), and many external people ask “how do you get alignment between teams?” or “every other company has them, why don’t you?”. My response has always been: if teams want to know something (vision or otherwise), they’ll ask, the SLT are partially responsible for getting the team aligned, and we’ve grown to 160+ people, $45M revenue, and are profitable, without these time-sucking company-wide calls. However, the retreat is an important opportunity for us to get the company excited, and most importantly, have everyone come away reminded that they’re working at a winning company, with a future that will impact hundreds of millions of people and help make the world more secure.
It’s why I believe the retreat contributes to employee retention. There is no data to back this up (in fact there is more against it than for it), but having staff understand where the company is headed, its achievements, our unique opportunity/position, and network with everyone else, helps reinforce TryHackMe’s culture and why our work is important.
On a personal note, one of the biggest drivers of us getting to $100M is scaling our B2B motion. As I spend a lot of time with B2C, and want to get closer to B2B, my main goal at this retreat was to learn as much about it as I could from the people closest to b2b. I actually sat in the hotel reception for most of the first day (when people were arriving) just to talk to as many people as I could, and got insights I doubt I’d have got over a call. I’d recommend going into any retreat or event with a few goals; it’s easy to default to small talk, but knowing what you want makes for much more meaningful conversations.
Hackathon
One of my favourite parts of this year’s retreat was our 1-day hackathon! We split the whole company into cross-functional teams of 4-6, so marketers were building alongside engineers, and gave each team one rule: build something totally new that solves a real challenge we’re facing as a company. Teams spent the day building, then had 60 seconds each to present. I had teams prepare before the retreat, so they had time to think through their idea before the hackathon started.
One important rule of the hackathon was that each team had to ship something. Demos were mandatory (a slide deck alone isn’t a demo), and they needed to show something people could actually see!
Here are some of my favourite projects that came out of the retreat:
Capture the job - an employee and employer portal to make recruitment easier. It gives students employment opportunities, but also makes hiring better for employers (saving them time and showing them the best candidates).
Recent Threats - a tool that keeps track of the software versions a client is running and alerts them as soon as a public vulnerability affecting one of those versions is disclosed.
Teacher/Manager Student Behaviour Insights - showing instructors and managers how a student has performed based on what they actually did (rather than just content completion), and identifying where a group of students or practitioners is weak by analysing their behaviour as a team.
Cards & collectables (see below for video demo) - a new game users can play on TryHackMe where they collect cards and use them in a virtual cyber game.
GOV/Military Game - a government/federal capability defense training game
KoTH Improvements - giving our King of the Hill competitive hacking game a full redesign, with AI generating fresh exercises on demand so no two games are the same.
There were too many great projects to list them all, but here are a few others that stood out: a TryHackMe MCP server, TryPrepMe (an interview preparation experience), a way to re-engage dormant clients, and many more.
The hackathon was a real success. Everyone I spoke to loved it, and I think it showed many of our non-technical staff what they can build with AI tools they don’t normally use. In 2026, everyone is a builder, especially at TryHackMe.
Introducing a hackathon was the biggest change to our 5th retreat, and it’s something we’ll now do every year. It also helps justify spending £400k on bringing everyone together in person.
Other quick reflections
There is so much I could write about our 2026 retreat, but here are a few additional notes on what I loved, what needs changing, and some unexpected learnings.
What I loved about this retreat
Being reminded how talented most of our people are
Listening to the award night winners acceptance speeches
Reflecting on how much we’ve achieved in 12 months
The intensity. This is something I said was missing about on our last company retreat (post). The structure of the retreat this year, with the hackathon and morning talks, worked really well.
What needs changing
With b2b being a big driver for us hitting $100M ARR, we should have had more discussions and breakout sessions on how we achieve this (especially as we plan for 2027).
I need to remind everyone about the insanely unique and special opportunity we have in front of us! We’re bootstrapped and profitable, and have spent 7 years laying the groundwork to scale to hundreds of millions of people.
Unexpected learnings
The downside of a retreat is lost momentum. Teams spend weeks preparing for the retreat, everything stalls while we're away, and then everyone has to restart.
How much creativity comes from being in person.
Just how much TryHackMe has influenced our competitors; being copied is the ultimate form of flattery
This year’s retreat was a good reminder of why I love my job. Over the years, TryHackMe has had a lot of acquisition offers, and we could sell up and move on. However, I really believe that (1) we’re critical to helping secure the digital world [imagine a world that has no cyber.. really think about it for a second..], (2) there is still so much to do, and we’re in a once-in-a-lifetime position [a brand millions learn on, a market position competitors copy, and an industry that will always need us: most companies never get one of those, and we have all three], and (3) I’m doing something I absolutely love, and I wouldn’t get the same sense of purpose anywhere else.
You’d be crazy to leave TryHackMe at our stage of growth... crazy! The chance to see a company go from $45M to $100 and beyond? No-one (iykyk) will stop us from building TryHackMe into the juggernaut it should deserves to be.
This years hats was “every second counts” - last year it was “unapologetically unconventional”.
I love the hats!
This was a fantastic, you've built something special Ben. I've had the privilege of meeting some of your team members on May and they're some of the nicest and smartest people I've met in our industry
onwards and upwards
Abed (unixguy)