Executive Assistant

TryHackMe is the world's biggest online cyber security training platform, with over 8 million users across thousands of businesses and schools. The company is fully bootstrapped, profitable, and has an entirely remote workforce focused on making the world more digitally secure.

As Executive Assistant to co-founder Ben, you will support a fast-paced leader deeply involved in product and software engineering. Your success will be measured by your ability to free up Ben's time and enable him to focus on high-impact priorities.

This is a generalist operator role rather than a typical assistant position. Calendar and inbox management represents less than 20% of the job. You will work directly with the co-founder to remove friction, solve problems quickly, and drive momentum across the business and occasionally in his personal life. The role is demanding, sometimes 24/7 in nature, and pivotal to the company's pace and success.

The position is fully remote but requires the successful candidate to be based in the UK and be willing to travel within the UK occasionally. Some availability beyond 5pm is expected.

Benefits include a dedicated work laptop and accessories, a £2,500 personal development budget, an annual company retreat, enhanced maternity and paternity benefits, and a 401k or pension scheme.

• Experience in a founder-facing, high-trust role such as Executive Assistant, Business Operations, Chief of Staff, or Founder's Associate.
• Experience working in a fast-paced startup or scale-up.
• Obsessively detail-oriented, operationally sharp, and unflinching under pressure.
• Strong instincts for what matters and the drive to act before being asked.
• Comfortable with ambiguity, fast pivots, and taking full ownership of outcomes.
• Genuine interest in product and how things are built.
• 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.
• Scrappy, urgent, and energised by fast-paced environments.
• Ability to work independently with minimal supervision.
• Fast communicator.
• Exceptionally high performance bar.
• Embraces AI.
• Willingness to be reachable beyond normal hours when needed.
• Must be based in the UK.

• Provide direct executive support to co-founder Ben and help optimise his time.
• Support department heads with partnership outreach, contractor coordination, ad hoc projects, and hiring.
• Help scale TryHackMe's expert-led live class workshop programme.
• Develop and manage a B2B client advisory board.
• Manage personal tasks such as scheduling appointments and handling ad hoc errands.
• Support other teams with administrative and operational tasks as needed.
• Remove friction, solve problems quickly, and drive momentum across the business.
• Travel within the UK occasionally when required.