Senior Red Team Operator: Adversary Emulation & AI Security

Citizens; Westwood (MA); Hybrid; USD 120,000 - 210,000; Full time

Benefits offered by this job

Flexible work arrangements

Medical, dental, vision coverage

Retirement benefits

Maternity and paternity leave

Education reimbursement

Wellness programs

Job summary

Citizens is seeking a Principal Operator, Red Team to lead offensive security engagements across on-premise, cloud, SaaS, and hybrid environments. You will emulate real-world attackers, identify attack paths, and drive improvements with defensive teams.

The role emphasizes full lifecycle testing, rigorous documentation, and collaboration across Purple Team activities. The position requires 4–8 years in red/purple team operations, strong scripting and tooling capabilities, and a deep

Qualifications

• Bachelor’s Degree in Security, Computer Science, Information Technology, or related field.
• Industry certifications such as OSCP, OSEP, CRTO, CRTP, or similar.
• Exposure to AI security testing or AI red teaming through hands on work, training, or research is preferred.

Responsibilities

• Execute Red Team and Purple Team engagements as a primary operator, including adversary emulation and intelligence driven attack paths.
• Design and execute campaign-based attack operations that simulate real-world adversary behavior across enterprise environments.
• Perform hands-on exploitation and abuse across on-prem, cloud, SaaS, and hybrid infrastructures.
• Collaborate with Detection Engineering and Blue Team to validate detections and refine response effectiveness.
• Translate offensive findings into actionable remediation insights and drive measurable risk reduction.
• Document findings with attack paths, control weaknesses, and detection gaps for engagement reports.

Skills

Red Team Operations

Adversary Emulation

Cloud & SaaS Attacks

AI Security Concepts

Purple Teaming

Threat Modeling

Education

Bachelor’s Degree in Security, CS, IT, or related field

OSCP / OSEP / CRTO / CRTP or equivalent

Job description

Citizens is seeking a Principal Operator, Red Team to lead offensive security engagements across on-premise, cloud, SaaS, and hybrid environments. You will emulate real-world attackers, identify attack paths, and drive improvements with defensive teams.

The role emphasizes full lifecycle testing, rigorous documentation, and collaboration across Purple Team activities. The position requires 4–8 years in red/purple team operations, strong scripting and tooling capabilities, and a deep