Lead Offensive Security Engineer

The College Board is a mission-driven organization dedicated to educational excellence, and they are seeking a Lead Offensive Security Engineer to enhance their cyber security operations. This role involves leading red team engagements, shaping offensive security strategies, and improving the organization's security posture through advanced penetration testing and threat simulations.

Responsibilities:

• Design and evolve the Red Team capability (35%)
• Define and continuously refine the red team engagement model, including methodology, scope development, rules of engagement, evidence standards, and quality controls
• Shape offensive assessment strategy in partnership with leadership, translating program priorities into technically sound attack approaches and campaign plans
• Determine tooling, infrastructure, and C2 frameworks used in approved environments, ensuring tradecraft reflects relevant real-world threat actors and techniques
• Establish standards for multi-stage adversary simulation, ensuring engagements are realistic, repeatable, and aligned to MITRE ATT&CK and current threat intelligence
• Continuously assess and improve how red team effectiveness is measured, including coverage, repeat findings, and defensive validation outcomes
• Lead execution of high-impact offensive campaigns (40%)
• Lead and personally execute advanced penetration tests and red team assessments across client applications, web applications, APIs, endpoints, and supporting infrastructure
• Orchestrate multi-stage attack simulations spanning initial access, privilege escalation, lateral movement, persistence, and objective completion within approved guardrails
• Plan and drive purple team exercises in close partnership with Threat Hunt, SOC, and Incident Response teams to validate and strengthen detection and response capabilities
• Evaluate the effectiveness of security controls, including SIEM, EDR, and network monitoring, and drive re-testing to confirm measurable improvement
• Coordinate and guide other red team engineers during engagements, ensuring consistency, technical rigor, and high-quality deliverables
• Drive measurable defensive impact and organizational enablement (25%)
• Translate offensive findings into prioritized, actionable remediation guidance and partner with system owners to drive meaningful risk reduction
• Produce executive-ready reports and briefings that clearly articulate risk, impact, and recommended actions for both technical and non-technical stakeholders
• Develop and maintain standardized red team artifacts, including playbooks, adversary emulation plans, reporting templates, and documentation that improve repeatability and knowledge transfer
• Provide technical guidance to Vulnerability Management and Threat Hunting teams on attacker behaviors, custom detection approaches, and validation techniques
• Foster a culture of collaboration and continuous learning across Cyber Operations teams through knowledge sharing, mentorship, and contribution to shared playbooks and best practices

Requirements:

• Demonstrated experience leading complex red team engagements or adversary simulations across applications, endpoints, APIs, and cloud environments
• Proven ability to influence technical direction and raise operational standards without formal people management authority
• 7+ years of experience in cybersecurity, with at least 3–5 years in offensive security, red team, or advanced penetration testing roles
• Deep hands-on expertise with modern C2 frameworks and adversary simulation tooling, with the ability to adapt tradecraft to evolving defensive controls
• Strong understanding of attacker methodologies, including MITRE ATT&CK, OWASP Top 10, CWEs, and real-world threat intelligence, and the ability to translate those into practical attack scenarios
• Experience conducting purple team exercises and validating SIEM, EDR, and network detection capabilities through controlled simulation and evidence-based testing
• Experience delivering executive-ready briefings that clearly communicate technical risk, business impact, and prioritized remediation actions
• High degree of discretion, integrity, and operational discipline when conducting sensitive offensive security work
• Bachelor's degree in Computer Science, Engineering, or equivalent practical offensive security experience
• Authorization to work in the United States without sponsorship
• Ability to travel 3-5 times a year to our NYC or Reston, VA office
• Proficiency in Microsoft Suite tools is preferred, though a willingness to learn is equally valued
• Curiosity and enthusiasm for emerging technologies, particularly AI-driven solutions, and a proactive approach to independently learning and applying new digital tools