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.