This is a unique opportunity to join as the technical co-founder of a new cyber security AI startup with all the unfair advantages for success: an enormous proprietary training dataset, a $2B market, and $1M in seed capital (backed by TryHackMe) to hit the ground running. Penetration testing companies today generate hundreds of millions in revenue, and we have a unique opportunity to capture the market with the data TryHackMe has. We’re looking for a technical co-founder that will have the full autonomy to build and scale the company day-to-day, with the full support of the TryHackMe founders.

Our edge in building the agent

• Labelled hacker user journeys – On TryHackMe, millions of people solve our labs. We have labeled user actions for each step they took: “executed X command → saw Y output → wrote Z script.” Across thousands of machines, this gives us millions of fully mapped user attack paths - essentially, a dataset of how real humans hack, in sequence. We believe we have the world’s largest labelled dataset of hacker behaviour to train AI agents on.
• TryHackMe’s Content & Labs - Access all TryHackMe’s training labs and virtual machines (>1000), which will be vital in initial model training.
• TryHackMe’s Influence - Although this is a seperate company, it’ll have the support of TryHackMe (THM), including introducing this agent into our training to be used by the next generation of practitioners. By drawing on our 5M users, thriving community, and enterprise clients, we can accelerate building the world’s most powerful pentesting agent.

What you get

• Growth and purpose - This will be one of the hardest but most rewarding things you’ll ever do. Expect huge personal and professional growth. For us as founders, building TryHackMe has been the most challenging and rewarding experience of our lives - and where we’ve learned the most.
• Work with us - TryHackMe bootstrapped to >$30M ARR and 140+ staff over 7 years. You will be working closely with the founders, learn lessons you wouldn’t get anywhere else.
• Equity and control - You’ll own a stake in the company and run day-to-day execution, with our close involvement in the early stages.

What we’re looking for

• All in and obsessed - If 60+ hours a week sounds painful, it’s not for you.
• Missionary, not mercenary - Compensation and equity are there, but the fuel is your drive to build something game-changing.
• One of the following:
  • Professional experience in cyber or AI - e.g. you’ve worked as a CISO, security researcher, or red/blue teamer. You understand how attackers think or how AI models are engineered, and you’ve shipped serious work.
  • AI/ML Engineer with a strong interest in cyber - you’ve trained, fine-tuned, or deployed models in production. You love building agents and experimenting with LLMs, and you’re hungry to apply that to offensive/defensive security.

The short, medium, and long term

• Short term - build an MVP with THMs $1M seed round and generate proof that the agent has potential. Then we expect we’ll raise to acquire the best talent and accelerate.
• Mid term - run with a deliberately small but exceptionally strong team, obsessively focused on making the agent world-class at one thing before expanding scope.
• End state - Its unclear, and we want you to help shape it. What matters first is building and proving the agent. Once it delivers credible results, we’ll decide how to scale and monetise - whether that’s as a tool for pentesters, or as a platform to disrupt the $2B pentesting-aaS market.

Apply

The mission is to build the most capable AI penetration testing agent and change how companies identify vulnerabilities. Threat actors are rapidly weaponising AI, and we must outpace them by detecting and exploiting weaknesses before they can.

The end state is intentionally open - once the agent works, we’ll decide together how to scale and monetise, whether as a tool for pentesters or as a platform to disrupt the $2B pentesting-as-a-service market. This is a rare opportunity: equity, ownership, and the chance to run a company from day one with the full backing of TryHackMe.