Head of Operations

Remote - UK or Europe

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.

The Role

TryHackMe operates like an elite sports team, has a performance-oriented culture, and is looking for an intense independent operator to lead HR (3), technical support (3), compliance and IT (1), finance (3) and partner with legal and TA (4).

What is most important for TryHackMe is that we're able to move fast by having operations support departments, not obstruct them; fewer policies and less process, not more, so people can focus on the work. Operations is the oil in our company engine. It's not the flashiest part of the machine, but nothing runs without it, and getting it right is what lets everyone else move fast.

It's critical that you agree with our culture and way of working, as TryHackMe is not for everyone, so make sure to read this article before applying. This position has a high degree of autonomy and will be critical in allowing us to scale further in a scrappy but sustainable way to grow beyond $100M ARR. You will report directly into Ben (the founder).

Primary Responsibilities include:

• Support AI transformation - Lead how TryHackMe operates in the AI-2026 era internally, identifying where AI can replace or accelerate operational work across all departments.

• Talent, Culture & Performance: Work with the recruitment team and department heads to attract, retain, and develop top talent, while actively driving and enforcing our performance-first culture.

• HR, EOR & Legal: Own HR operations, EOR admin (Remote.com), and employee relations across our fully distributed, multi-country workforce, partnering with legal to reduce risk and escalating only genuine exceptions.

• Compliance & IT Operations: Own Vanta/SOC2 and the audit/ISO cycle end to end, IT operations, technical support, and access management across our tools.

• Financial Management: Own the finance function alongside a Financial Controller, driving budgeting, holding teams accountable, and proactively identifying cost-saving opportunities across the business.

This role is not right if you:

• Default to building a new system rather than finding the fastest path through

• Need your departments work recognised publicly to feel it matters

• Like to layer teams, rather than keeping it flat until it's unsustainable

• Don't like being in the details, or get uncomfortable being scrappy

• Measure success by team size, rather than by how much you can do with less

• Aren't competitive, clock-watch, or like to log off bang on 5pm

• Want frequent input and direction from Ben

Requirements

• 3+ years running HR and business operations, with experience working closely alongside finance

• Experience owning IT operations and business systems, including access management, tooling, and vendor management

• Startup/scale-up experience in fast-paced, constantly changing SaaS/Tech environments

• Managed operations for a global workforce

• Demonstrable AI use in ops work

Benefits & Perks

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

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

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

🍕Lunch on us - whether you're a pizza-lover, salad obsessed or a big sushi fan, TryHackMe will cover the cost of your lunch order during our recurring company virtual lunches.

🧡 Health Insurance - if you're in a country that doesn't have public health care.

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

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

Hiring Process

• Stage 1 (15m): Screening call with the recruitment team or Ben

• Stage 2 (30m): Scenario-based questions

• Stage 3 (45m): Meet face-to-face in (or near) London

• Stage 4 (30m): Round table quick fire interview with our SLT