Executive Assistant

TryHackMe; United Kingdom; Remote; GBP 40,000 - 50,000; Full time

Job summary

A fast-growing cyber security training platform is seeking an Executive Assistant to work closely with the co-founder. This role involves project management, supporting department heads, and engaging in a dynamic startup environment. Candidates should have over 3 years in a high-trust role, strong research skills, and thrive in fast-paced settings. The position offers a competitive salary package and the flexibility to work remotely.

Benefits

Salary: £40,000 – £50,000

100% Remote

£2,500 personal development budget

Annual fully-paid company retreat

Health insurance where applicable

Enhanced maternity & paternity package

401k / Pension options

Company virtual lunches

Free subscription for family and friends

Qualifications

• 3+ years in a founder-facing, high-trust role.
• Experience in a fast-paced startup or scale-up.
• Operationally sharp and unflinching under pressure.

Responsibilities

• Manage cross-functional projects.
• Organise user calls and document insights.
• Support department heads with diverse tasks.

Skills

Experience in executive support role

Strong research skills

Attention to detail

Ability to work independently

Fast communication

Interest in product development

Job description

TryHackMe is the fastest-growing online cyber security training platform. Our mission is to make the world more digitally secure through gamified security lessons and challenges. We have grown to more than 6 million users and our growth continues.

The Role

This isn’t a typical assistant role - calendar and inbox management is less than 30% 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, acts decisively and doesn’t hesitate to get stuck into anything needed to move the company forward. The role is demanding and can be 24/7 in nature, absolutely pivotal to the pace and success of the business.

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

• Manage a cross-functional project (via a project manager) that Ben is deeply involved in, coordinating across five teams.
• Organise user calls from specific segments, document key insights, and share them with relevant teams.
• Provide support to department heads on a diverse range of tasks, including partnership outreach, coordinating with contractors on ad-hoc projects, and hiring.
• Understand priorities, develop playbooks and automate repetitive tasks.
• Manage personal tasks to optimise time, such as scheduling appointments, turning blog drafts into polished posts with artwork, and handling ad hoc errands.

We’re a 150-person startup, so you’ll handle anything and everything — the scope is massive. Must be happy to travel within the UK occasionally.

About You

• 3+ years of 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.
• 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.

Skills & Requirements

• 3+ years of experience in an executive support role.
• 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 chaotic 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.
• Excited by working with high-intensity founders.

Benefits & Perks

• Salary: £40,000.00 – £50,000.00
• 100% Remote – Work from anywhere in a fully digital world.
• Tools – a dedicated work laptop and any accessories you need.
• Swag Pack – start your TryHackMe journey with a branded swag bundle.
• Personal Development – £2,500 training budget for certifications, books and more.
• Company Retreat – annual retreat, fully paid for by us.
• Health Insurance – for countries without public health care (where applicable).
• Enhanced Maternity & Paternity – an enhanced package on top of statutory requirements.
• 401k / Pension – retirement savings options.
• Lunch on us – company virtual lunches and meals during events.
• Free THM subscription for your circle – extend the platform’s impact to family and friends.

Hiring Process

• Stage 1 (10m): HireFlix one-way interview / questioning
• Stage 2 (20m): Phone screen
• Stage 3 (30m): Short task
• Stage 4 (45m): Final interview

TryHackMe isn’t for everyone. Read the related article before applying. TryHackMe takes the pain out of learning and teaching cyber security by offering prebuilt courses with VMs hosted in the cloud. Our platform is suitable for CTFs, workshops, assessments, or training. We launched in 2018 and now have over six million users on the platform.