We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.

Red Team / Adversarial Simulation Engineer

The Opportunity

We’re hiring a Red Team / Adversarial Simulation Engineer to help strengthen our offensive security capabilities. You’ll support adversary simulation exercises and targeted testing mapped to MITRE ATT&CK, working alongside team members to identify risk and help improve defenses.

You’ll work closely with senior Red Team operators and security engineering partners to execute scoped exercises, produce clear evidence of exploitable paths, and translate offensive findings into practical risk reduction.

What You’ll Do

• Support operations: Assist in planning and execution of approved adversary simulation exercises across endpoints, identity, applications, cloud, and third-party integrations, with guidance from senior operators.
• Execute adversary tradecraft: Operate across initial access simulation, internal discovery, credential access testing, privilege escalation, lateral movement, command-and-control simulation, and objective-based actions within approved scope.
• Map procedures and findings to MITRE ATT&CK to keep tradecraft, reporting, and scenario design consistent across exercises.
• Track operational outcomes: Collect command output, screenshots, logs, timelines, access paths, affected assets, and constraints so findings are defensible and reproducible.
• Build technical depth: Help maintain lab environments, test infrastructure, and approved tooling while following established safety and OPSEC practices.
• Learn and share tradecraft: Contribute to team standards, document lessons learned, and participate in peer reviews of techniques, findings, and reports.
• Apply and assess LLMs: Use LLMs to support authorized offensive security operations, including research, scripting, analysis, tooling, and workflow automation, and evaluate LLM-enabled systems for weaknesses that could contribute to an attack path.
• Follow safety and compliance practices: Operate within defined scope, approvals, deconfliction steps, and engagement rules for all activities.

What You Bring

• Experience: 1 to 3 years in offensive security, penetration testing, Red Team operations, adversary simulation, or hands-on security engineering with offensive testing exposure.
• Technical foundation: Solid working knowledge of Windows and Linux internals, cloud security, AI/LLM, common enterprise attack paths, and at least one major cloud platform such as AWS, Azure, or GCP.
• Framework fluency: Practical familiarity with MITRE ATT&CK, including the ability to map and demonstrate Red Team procedures against tactics, techniques, objectives, and enterprise risk.
• Scripting and tooling: Practical experience writing or modifying scripts in PowerShell, Python, Go, Rust, or C#, with enough depth to automate operator tasks, adapt approved tooling, handle output, and troubleshoot execution issues.
• Operator mindset: Ability to think through attack paths, adjust safely when assumptions fail, maintain discipline under scope constraints, and document what worked, what failed, and why.
• Communication: Clear technical writing, disciplined evidence handling, and the ability to explain attack paths, impact, and remediation context to technical audiences without overstating findings.
• Automated security testing: Experience planning and managing test execution across a range of automated security testing tools, validating results, tracking coverage, and delivering clear, actionable reports.

Certifications (nice to have): OSCP, CRTO/CRTP, or similar hands-on security certifications.

About Us | Our Culture | What It’s Like to Work Here