Executive Assistant

TryHackMe is the world's biggest online cyber security training platform, with over 8 million users across thousands of businesses and schools. We've never raised funding, are fully bootstrapped at >$40M in revenue (2026), profitable, and have a 160-person, entirely remote workforce. Our mission is to make the world more digitally secure.

You’ll be the Executive Assistant (EA) to the co-founder, Ben, and will play a critical role in supporting a fast-paced leader who is deeply involved in product and software engineering. This is a unique opportunity to work closely with one of the founders of a bootstrapped and rapidly growing startup. Success in this role will be measured by your ability to effectively free up Ben's time, enabling him to focus on high-impact priorities.

The Role

This isn’t a typical assistant role - calendar and inbox management is less than 20% of the job. As an EA, you’ll be embedded into the engine room of the company - partnering directly with co-founder Ben to remove friction, solve problems fast and drive momentum across all corners of the business and sometimes in his personal life too.

You’ll be a generalist operator: someone who thrives in chaos and brings it to a calm and controlled state, acts decisively and doesn’t hesitate to get stuck into anything needed to move the company forward. The role is demanding, sometimes 24/7 in nature and absolutely pivotal to the pace and success of the business.

Here are some things you’ll do in your first few months

• Provide support to department heads on a diverse range of tasks, including partnership outreach, coordinating with contractors on ad-hoc projects, and hiring.

• Help scale up TryHackMe’s expert-led live class workshop programme

• Develop and manage a B2B client advisory board

• Manage personal tasks to optimise time, such as scheduling appointments, and handling ad hoc errands.

• Be ready to support any other team with admin or operational tasks.

We’re a fast-moving company, so you’ll handle anything and everything - the scope is massive. Must be happy to travel within the UK occasionally.

About You

• Experience in a founder-facing, high-trust role (EA, BizOps, Chief of Staff, Founder’s Associate etc).

• Have worked in a fast-paced startup and/or scale-up previously.

• Obsessively detail-oriented, operationally sharp and unflinching under pressure.

• Strong instincts for what matters and the drive to act on it before being asked.

• Excited by ambiguity, fast pivots and taking full ownership of outcomes.

• Genuinely interested in product and how things get built.

• A natural work-life integrator, happy to be reachable beyond normal hours when needed. Ben often works into the evenings, so some availability beyond 5pm should be expected.

Skills & Requirements

• 5+ years of experience in an executive support role.

• Excited by working with high-intensity founders.

• Strong research skills for quickly finding, verifying and summarising information.

• High attention to detail and accuracy in managing tasks and communications.

• Operates scrappy, acts with a sense of urgency and is energised by fast paced environments.

• Ability to work independently with minimal supervision.

• Fast communicator (Ben tends to talk quite fast and squeezes a lot into 15m daily calls)

• Has exceptionally high performance bar.

• Embraces AI

Benefits & Perks

🚣 100% Remote - In a fully digital world, work from anywhere you want!

💻 Tools - a dedicated work laptop + any accessories you need to do your best work.

💪 Personal Development - £2,500 training budget to acquire certifications, books and more.

⛱️ Company Retreat - an annual company retreat, fully paid for by us!

🍼 Enhanced Maternity & Paternity- an enhanced package on top of statutory requirements.

💸 401k / Pension - TryHackMe makes it easy to save money for your retirement

Our Hiring Process:

• Stage 1 (10m): Application process / video answers

• Stage 2 (20m): 1st interview

• Stage 3 (30m): Short task

• Stage 4 (45m): Final interview

TryHackMe isn’t for everyone, and you should read this article before applying.