Offensive Security Lead

8+ years in offensive security, with demonstrated hands-on experience in both penetration testing and red team/adversary emulation — not just one discipline.

2+ years directly managing or leading offensive security teams, ideally within a regulated industry (financial services, fintech, healthcare, or similar).

Proven experience designing and implementing AI-led or AI-assisted offensive security programs — you can speak concretely to what you built, what tooling/models you used, what scaled and what didn't, and how it changed team output.

Deep technical fluency across network, web/application, cloud (AWS/GCP/Azure), and mobile attack surfaces, plus familiarity with adversary emulation frameworks (e.g., MITRE ATT&CK) and C2 tooling.

Track record of building programs from the ground up or maturing existing ones — process, tooling, metrics, and team structure, not just individual engagements.

Strong written and verbal communication skills; comfort presenting findings and program strategy to engineering leaders, risk teams, and executives.

operating in a highly regulated environment and working with auditors/examiners is a strong plus.

Relevant certifications (OSCP, OSCE, OSEP, GPEN, GXPN, CRTO, or equivalent demonstrated experience) preferred but not required in lieu of strong hands-on track record.

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Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

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