Head of Operations

TryHackMe; Greater London; Remote; GBP 110,000 - 170,000; Full time

Benefits offered by this job

100% Remote

Personal Development £2,500 training

Company Retreat

Lunch on us

Health Insurance

Enhanced Maternity & Paternity

401k / Pension

Job summary

TryHackMe is seeking an autonomous leader to head HR, business operations, IT, compliance, and finance for a fully distributed workforce across the UK/Europe. The role collaborates with legal and TA to scale while maintaining a performance-first culture.

You will drive AI transformation, own EOR workflows, and manage multi-country operations with a focus on speed, low friction processes, and cost efficiency.

Qualifications

• 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.

Responsibilities

• Lead HR, operations, IT, and finance interfaces across multi-country workforce.
• Drive AI transformation and operational efficiency across departments.
• Own compliance and IT operations, including vendor management and audits.
• Oversee budgeting and cost-saving initiatives across the business.
• Partner with legal and talent acquisition to scale rapidly and sustainably.

Skills

HR leadership

Operations management

Finance collaboration

Vendor management

SaaS/Tech experience

AI in ops

Job description

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.

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

TryHackMe takes the pain out of learning and teaching cyber security. Our platform makes it a comfortable experience to learn by designing prebuilt courses that include virtual machines (VM) hosted in the cloud and ready to be deployed. This avoids the hassle of downloading and configuring VMs. Our platform is perfect for CTFs, Workshops, Assessments, or Training. We've come a long way since launching in 2018, with over 8 million users on the platform!