Penetration Tester

Help us build the future of penetration testing.

Pensure.ai is building a different kind of cyber security company. Backed by OIF Ventures - we're creating an AI-powered offensive security platform that combines autonomous AI agents with experienced human operators - delivering penetration testing at a scale, speed and consistency that wasn't previously possible.

We're not trying to replace penetration testers. We're building the world's best AI-powered platform to make them dramatically more effective. Every customer assessment should leave the platform smarter than it was yesterday.

We're looking for a penetration tester who wants to help make that happen.

About the role

Firstly, this isn't a traditional Pentesting role.

You'll split your time between two things that feed each other:

• Running real customer assessments on Pensure's AI platform - scoping, running the AI harness, supervising agent behaviour, validating findings, expanding attack paths through manual testing, verifying exploitability, and presenting to customers.
• Making the platform better - spotting where the AI succeeds and where it struggles, improving prompts and agent behaviour, building new attack playbooks, cutting false positives and hallucinations, and working with engineering to turn your ideas into product.

If you find yourself doing the same thing twice, your first instinct should be: "How do we teach the platform to do this instead?"

And finally - this role is designed to grow.

Initially, you’ll split your time between customer work and product improvement.

Over time, we expect the balance to shift.

As the AI platform becomes more capable, you’ll spend less time performing repetitive testing and more time improving the product, designing new offensive techniques and shaping the future of AI-assisted penetration testing.

Strong performers will have opportunities to grow into technical leadership as Pensure scales.

What we're looking for

We care far more about how you think than about ticking every box. You probably have a background in some of these areas:

• Penetration testing, offensive security, red teaming, security research, bug bounties, CTFs, or building security tooling - anything where you broke a system because you wanted to understand it.

You'll be great at this if you

• Love pulling systems apart and thinking creatively about attack paths.
• Automate repetitive work by instinct.
• Can explain technical problems clearly and enjoy working directly with engineers.
• Use AI every day to make yourself more effective.
• Are opinionated, but change your mind when the evidence is better.

Highly regarded experience (desired, not essential)

• Web application testing
• API security
• Small and medium enterprise networks
• OSINT
• Burp Suite, Caido or similar tooling
• Python, Bash or PowerShell scripting
• AI coding assistants
• Prompt engineering
• Building automation
• Writing your own security tooling
• Certifications like OSCP, CREST or CRTO are a plus - not mandatory. If you've built interesting things or found interesting vulnerabilities, we'd rather hear about those.

How we work

You’ll have a high degree of trust, autonomy and ownership from day one.

We don’t believe in managing every hour of your day or telling you exactly how to solve a problem.

We hire smart people, give them context and expect them to make good decisions.

If something is broken, fix it. If you think there’s a better way, build it. If you can automate repetitive work, automate it.

And if you disagree with a technical decision, challenge it. Healthy debate makes the product stronger. Leave the platform better than you found it. Every day.

What's next?

If you're excited about this opportunity and feel it's a great fit for your skills - we'd love to hear from you! Please go ahead to apply direct. If you have any questions, you're also welcome to reach out to Pam Stevenson who works with one of our investors (OIF Ventures) and is helping with recruitment (Sign in to view email)