Senior Manager, Offensive Security

Vanguard•Malvern, PA

23h•Hybrid

About The Position

The Senior Manager, Offensive Security leads our advanced offensive security program within the Offensive Security & Fraud Testing (OSFT) team. This role oversees all offensive security operations – including full-scope Red Team engagements, targeted penetration testing, AI-augmented offensive security initiatives – with the mission of proactively identifying vulnerabilities and strengthening the organization’s defenses. Success in this role is measured by the maturity and impact of our offensive security program: meaningful risk reduction, improved detection & response capabilities, strong stakeholder trust, and continuous team development.

Requirements

10+ years in penetration testing, red teaming, or adversary simulation, with proven success as a hands-on operator delivering high-impact engagements.
Deep knowledge of network, application, and cloud security vulnerabilities, exploitation techniques, and attacker methodologies (MITRE ATT&CK, kill chain, etc.).
3+ years of experience leading offensive security teams or programs.
Demonstrated ability to manage and develop high-performing teams, including setting goals, mentoring senior engineers, and attracting top talent.
Skilled in strategic planning and multi-project management – able to prioritize and allocate resources to meet objectives across simultaneous operations.
Exposure to or strong interest in AI/ML technologies and security automation.
Understand how generative AI and tools like LLMs can be leveraged in offensive security (e.g. for recon or automating tasks).
Experience overseeing or implementing innovative solutions (like advanced scripting, C2 frameworks, or integrating AI agents) in security testing is a plus.
Excellent communication skills with both technical and executive audiences.
Able to clearly articulate risk and influence senior stakeholders to take action on security findings.
Experience collaborating with defensive security teams, fraud/risk teams, and engineering groups to drive remediation and improve security posture.
A track record of building trust and credibility through transparency and consistency in execution.
Bachelor’s degree in Computer Science, Cybersecurity, or related field (or equivalent experience).
Relevant certifications (e.g., OSCP,CISSP, GIAC GPEN, CRTO) that demonstrate both offensive technical depth and security management knowledge are strongly preferred.

Nice To Haves

Experience overseeing or implementing innovative solutions (like advanced scripting, C2 frameworks, or integrating AI agents) in security testing is a plus.
Relevant certifications (e.g., OSCP,CISSP, GIAC GPEN, CRTO) that demonstrate both offensive technical depth and security management knowledge are strongly preferred.

Responsibilities

Define and drive the strategic vision for offensive security testing, translating high-level cyber risk objectives into actionable testing plans and operations.
Establish annual roadmaps for red teaming, and pen testing exercises aligned with emerging threats and business priorities.
Lead and coach a geographically distributed team of offensive security professionals.
Oversee hiring, performance management, and skill development, ensuring a high-performing, collaborative culture.
Foster innovation within the team by encouraging the adoption of new techniques (e.g., AI-driven tools) and by mentoring staff in advanced offensive tradecraft.
Plan, scope, and approve complex offensive engagements such as Red Team operations ensuring they are conducted safely, ethically, and with clear goals.
Oversee GenAI-enabled offensive security projects, setting guidelines for responsible use of AI/automation as force multipliers in our operations.
Provide hands-on guidance when needed, leveraging your own red team experience to support critical operations or complex exploit development.
Coordinate Purple Team exercises that bring together our offensive team with CSOC Team and fraud teams to test and improve detective controls.
Serve as the primary liaison with defensive stakeholders, ensuring findings are immediately actionable and bridging gaps between offense and defense.
Champion a partnership approach – sharing threat intelligence, aligning on TTPs (Tactics, Techniques, Procedures) to emulate, and jointly prioritizing remediation efforts.
Ensure comprehensive documentation and communication of all offensive testing activities and outcomes.
Review and finalize detailed reports for each engagement, highlighting identified vulnerabilities, their business impact, and recommended fixes.
Present program results and risk insights to senior security leadership and risk governance forums.
Continuously refine methodologies, enforce adherence to frameworks (e.g., MITRE ATT&CK, internal policies), and track metrics to measure program effectiveness (coverage of attack surface, detection rates, time-to-remediation, stakeholder satisfaction).
Identify opportunities to expand or enhance the program – such as integrating new offensive techniques, improving automation, or refining Purple Team processes – and drive these initiatives to increase program maturity.
Stay current on industry trends and ensure our team remains at the forefront of offensive security practices, especially regarding AI augmentation, cloud security, and evolving threat landscapes.