Senior Red Team Lead - AI-Driven Adversary Emulation

Citizens; Boston (MA); On-site; USD 170,000 - 230,000; Full time

Benefits offered by this job

Competitive benefits

Flexible work arrangements

Job summary

Citizens in Boston is seeking an Offensive Security Manager (Red Team) to lead the enterprise red team, simulate real world cyber threats, including AI-enabled attack scenarios, and drive measurable improvements in detection, response, and resilience.

Reporting to Cyber Security leadership, you will manage a team of offensive security professionals, collaborate across operations, risk, and tech functions, and evolve the program with risk-based testing and adversary emulation.

Qualifications

• Bachelor's degree or equivalent in Cybersecurity, CS, IT, Engineering, or related field.
• 8+ years in cybersecurity with 5+ years in offensive security or Red Team.
• 3+ years of people leadership managing security engineers/Red Team practitioners.
• Experience leading complex Red Team and Purple Team engagements with intelligence driven campaigns.
• Strong understanding of attacker methodologies and modern offensive security frameworks.

Responsibilities

• Own and evolve the enterprise Red Team program, including adversary emulation, threat-informed testing, and advanced offensive security assessments.
• Lead, mentor, and develop a team of Red Team professionals through hiring, performance management, coaching, and career development.
• Design and execute realistic Red Team and Purple Team engagements, including assumed breach scenarios and AI-related attack simulations.
• Assess risks from AI, automation, and data-driven systems and incorporate them into testing strategies.
• Ensure all Red Team activities are conducted safely, ethically, and with defined guardrails.

Skills

Offensive security

Red Team operations

Leadership

Threat emulation

Communication

Education

Bachelor's degree or equivalent in Cybersecurity/CS/IT/Engineering

Tools

Adversary emulation tools

AI security testing tools

Job description

Citizens in Boston is seeking an Offensive Security Manager (Red Team) to lead the enterprise red team, simulate real world cyber threats, including AI-enabled attack scenarios, and drive measurable improvements in detection, response, and resilience.

Reporting to Cyber Security leadership, you will manage a team of offensive security professionals, collaborate across operations, risk, and tech functions, and evolve the program with risk-based testing and adversary emulation.