Offensive Security Lead

What you'll do

• Unify Penetration Testing and Red Team into a single, cohesive Offensive Security function with shared standards and tradecraft.
• Develop and execute an offensive security roadmap aligned with the company's risk profile and regulatory obligations.
• Design and implement AI-augmented tools and workflows to accelerate reconnaissance, exploit development, and report generation.
• Lead and contribute to technical engagements including network, application, cloud, and adversary emulation operations.
• Hire, coach, and mentor a team of penetration testers and red team operators while establishing clear career paths.
• Define and report program metrics regarding coverage, finding severity, remediation velocity, and overall ROI to leadership.
• Collaborate with internal teams like SOC and Engineering to ensure offensive findings result in actionable remediations.
• Manage third-party vendors for pentesting tools and execution while overseeing budget and quality.

What we're looking for

• Must have 8+ years of experience in offensive security including both penetration testing and red team/adversary emulation.
• Must have 2+ years of experience directly managing or leading offensive security teams, preferably in a regulated industry.
• Must have proven experience designing and implementing AI-led or AI-assisted offensive security programs.
• Must possess deep technical fluency across network, web, application, cloud (AWS/GCP/Azure), and mobile attack surfaces.
• Must have a track record of building or maturing offensive security programs including process, tooling, metrics, and team structure.
• Must possess strong written and verbal communication skills to present findings and strategy to executives and risk teams.
• Experience operating in highly regulated environments and working with auditors is preferred.
• Relevant certifications such as OSCP, OSCE, OSEP, GPEN, GXPN, or CRTO are preferred but not required.