Winning the market with a company retreat

Understand why TryHackMe hosts a fully-inclusive company retreat for all staff once a year, and what I learned by investing £270k into our people for this year’s retreat.

TryHackMe is a fully remote company with staff all over the world, and every year we have a company retreat that brings everyone together, in person, for a full week of workshops and activities. This year it was hosted in Italy with 70 (of our >100) staff that travelled from 30+ countries to attend. The retreat has many benefits, albeit hard to tangibly measure, that makes spending £270k running it worth it. Heres why.

TryHackMe is in an unusual position where there is no clear winner in our market. We believe it’s open for the taking, but we must act now. The only way we will win the market is by rallying our troops behind our mission and taking advantage of this opportunity. The company retreat is a great way to do this.

Lets start off by going over the retreats structure.

• Sunday - The presentation outlines how everyone can get the most out of the retreat, celebrates accomplishments, and discusses notable stories from 2024. It ends with an icebreaker before dinner.

• Monday - We interview one of our users who transitioned from being a nurse to a cyber practitioner using the platform (more on this later), followed by a session from the founders on the next 1-3 years. The morning concludes with cross-functional workshops. In the afternoon, there is a fun team-building activity, followed by an off-site evening dinner.

• Tuesday - We have a motivational guest speaker, Colin Maclachlan (a former member of the SAS), who will talk about urgency, intensity, and drive. This is followed by insights from marketing, and the morning concludes with an AMA with the senior leadership team. The afternoon includes a beach activity with plenty of social time.

• Wednesday - This day is dedicated to teams, with department-specific workshops and social activities. The day (and retreat) concludes with an awards dinner, recognizing standout staff members.

You can check out our full agenda here.

It's rare that we all have the time to come together, step back, and really look at where we’re heading as a company, as well as the impact we’re making. The retreat is structured to encourage social interaction (especially between different departments – as a PLG company, it’s imperative that teams across the company form strong bonds) and to get everyone excited about the company’s direction.

Senior Leadership Team Ask Us Anything

There are so many reasons why I love the retreat, but if I were to summarise it:

• We work very cross-functionally at TryHackMe, and the retreat allows teams to meet face-to-face to build rapport and form better working relationships, which leads to stronger internal functions.

• It’s a rare opportunity to informally discuss and reflect on key projects (during breakfast, lunch, dinner, activities, on the coach, etc.).

• Everyone at TryHackMe has a unique perspective on their contributions to our mission, and we can use this time to talk to everyone individually to ensure we’re working on the right priorities for 2025.

• We can also recognize high-performing staff, showing others what excellence looks like and encouraging positive behavior and drive through healthy competition.

• Personally, I get the chance to talk to everyone, which serves as an informal in-person skip level. It helps me make better decisions and speeds up projects by staying connected to what’s happening on the ground.

• We align the company on our vision, key projects, and overarching mission.

I was so proud to invite one of our users to our retreat. Chrissy, who was a nurse, used TryHackMe to become a cyber practitioner and shared her story with the entire company. We spend a lot of time discussing numbers and growth, so it’s important to remind everyone that there are real humans behind the screen. Having staff see the impact of their work through compelling stories is crucial, and Chrissy was kind enough to join us at the retreat, allowing staff to talk to her about her journey.

User interview with Chrissy and our Head of Marketing

We were also joined by Colin Maclachlan from the SAS ("Who Dares Wins"), who spoke to us about his military missions and why it's important to act now. Urgency, intensity, and drive are the reasons you win—an ethos TryHackMe abides by. Colin's inspiring talk emphasized this message and was a hit with staff.

There were many organic conversations about what we’re building and aiming to achieve. Some breakfasts and lunches were spent in small teams discussing the next phase of development for key internal projects, ranging from new product experiences we’re building to big bet ideas planned for next year.

Collaboration is essential at TryHackMe. For example, our product teams work cross-functionally with software engineers, designers, marketing, content engineers, and more. Effective collaboration fuels creativity, drives innovation, and leads to better outcomes. This retreat is an opportunity to strengthen those connections and continue growing together as a team. During the retreat, teams were mixed up, giving everyone the opportunity to collaborate with different people each time. We did this through:

• Meals - Shared meals created informal opportunities for staff to connect, brainstorm, and build relationships across departments. It’s always a great sign when people want to stay out after dinner to continue socializing.

• Activities - Team-building activities encouraged problem-solving and collaboration, helping to break down silos and foster trust.

• Workshops - Our workshops had different focuses, involving different groups of departments.

• Travel - Some activities required travel via coach, which provided another small opportunity for people to have organic conversations in a relaxed environment.

Images taken by employees from the awards night, a lock-picking challenge, and raft beach challenge.

The retreat is expensive and logistically challenging, but worth it. We invest in our people, and know they’ll return it back 10x. TryHackMe only hires A players, and this company-wide benefit ensures we continue to keep our team excited, intensely aligned, bought into our mission and hyper focused on winning.

Now everyone has met, they should work better together, make better decisions, be more comfortable acting faster, which ultimately will help us win the market.

Here are a few posts from our team following this years retreat

Like what you read? We’re hiring: https://tryhackme.com/work-at-thm. We’re desperately in need of talented engineers and product managers:

• Growth Product Manager

• Associate Product Manager

• Senior Software Engineer

• Lead Software Engineer