Principal Red Team Operator

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

Principal Operator, Red Team

Role Summary

The Operator, Red Team is a hands on offensive security practitioner responsible for executing advanced adversary emulation and continuous red teaming operations across a modern, cloud and AI enabled enterprise. This role plays a critical part in building and scaling the organization?s offensive security capability and ensuring the company stays ahead of emerging threats in an evolving risk landscape.

Operating within high impact engagements, this individual will simulate real world attackers, identify and validate attack paths, and partner closely with defensive teams to ensure findings translate into measurable improvements in detection, response, and overall risk posture. Success in this role requires deep technical tradecraft, strong operational discipline, and a mindset focused not just on breaking systems, but on strengthening them through full lifecycle accountability.

This role reports to the Red Team Manager and works closely with Blue Team, Detection Engineering, Threat Intelligence, and Incident Response through Purple Teaming to continuously improve defensive effectiveness.

Locations and Work Arrangement

Candidates must be willing to commute to one of the following hub locations with a hybrid schedule and flexibility across the listed hubs. We are open to supporting relocation assistance for highly qualified candidates who are not currently located near one of these offices:

• Johnston, RI
• Boston, MA
• Iselin, NJ
• Pittsburgh, PA
• Plano or Irving TX
• Phoenix, AZ
• Charlotte, NC
• Manchester, NH
• Cleveland, OH

Key Responsibilities

• Execute Red Team and Purple Team engagements as a primary operator, including adversary emulation, assumed breach scenarios, 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
• Simulate advanced attacker tradecraft, including living off the land techniques, identity abuse, privilege escalation, lateral movement, persistence, command and control, and controlled data exfiltration
• Conduct testing against AI enabled systems and workflows, including abuse and misuse of AI assistants, copilots, and automation platforms
• Execute prompt manipulation, indirect prompt injection, and AI model misuse scenarios to evaluate emerging attack surfaces
• Collaborate closely with Detection Engineering and Blue Team during Purple Team engagements to validate detections, identify coverage gaps, and refine response effectiveness
• Translate offensive findings into actionable remediation insights and partner with stakeholders to ensure vulnerabilities are addressed and control effectiveness is improved
• Contribute to full lifecycle execution of engagements, ensuring findings are tracked through resolution and result in measurable risk reduction
• Leverage and extend red team tooling and frameworks and develop targeted scripts or payloads to emulate specific adversary behaviors
• Document findings clearly, including attack paths, control weaknesses, and detection gaps, contributing to engagement reports and technical debriefs
• Operate within defined rules of engagement, safety protocols, and ethical guidelines to ensure realistic and controlled testing
• Stay current on evolving adversary tactics, offensive tooling, and AI security research, incorporating new techniques into ongoing testing efforts

Experience and Skills

• 4 to 8 years of hands on cybersecurity experience with a strong focus on Red Team operations, adversary emulation, or advanced offensive security
• Demonstrated experience executing Red Team or Purple Team engagements in assumed breach or adversary based scenarios
• Proven ability to design and execute attack paths rather than relying solely on automated tools or point in time testing
• Strong technical capability across multiple attack surfaces, including identity and access attacks, endpoint and network exploitation, cloud and SaaS environments, and command and control frameworks
• Understanding of campaign based red teaming and continuous testing approaches, including iterative and regression style validation
• Working knowledge of AI security concepts, including how AI enabled systems, inputs, and workflows can be manipulated or abused
• Ability to collaborate with Blue Team and Detection Engineering to translate offensive activity into improved detection and response capabilities
• Strong operational discipline, including clear documentation, safe execution, and adherence to engagement constraints
• Effective communication skills, with the ability to explain technical findings to security practitioners and cross functional partners
• Demonstrated curiosity, adaptability, and ability to operate in rapidly evolving threat and technology environments

Education and Certifications

• Bachelor?s Degree in Security, Computer Science, Information Technology, or related field, or equivalent experience
• Relevant industry certifications such as OSCP, OSEP, CRTO, CRTP, or similar advanced offensive security credentials
• Exposure to AI security testing or AI red teaming through hands on work, training, or research is preferred

Pay Transparency

The salary range for this position is from $120,000 to $210,000 per year, plus an opportunity to earn an annual discretionary bonus. Actual pay is based on various factors including but not limited to, the budget, work location, relevant skills, and experience.

Some job boards have started using jobseeker-reported data to estimate salary ranges for roles. If you apply and qualify for this role, a recruiter will discuss accurate pay guidance.

We offer competitive pay, comprehensive medical, dental, and vision coverage, retirement benefits, maternity and paternity leave, flexible work arrangements, education reimbursement, wellness programs, and more. Citizens? paid time off policy exceeds the mandatory paid sick or paid time away policies of local and state jurisdictions in the United States. For an overview of our benefits, visit our Careers site -

Equal Employment Opportunity

Citizens, its parent, subsidiaries, and related companies (Citizens) provide equal employment and advancement opportunities to all colleagues and applicants for employment without regard to age, ancestry, color, citizenship, physical or mental disability, perceived disability or history or record of a disability, ethnicity, gender, gender identity or expression, genetic information, genetic characteristic, marital or domestic partner status, victim of domestic violence, family statparenthood, medical condition, military or veteran status, national origin, pregnancy/childbirth/lactation, colleague?s or a dependent?s reproductive health decision making, race, religion, sex, sexual orientation, or any other category protected by federal, state and/or local laws. At Citizens, we are committed to fostering an inclusive culture that enables all colleagues to bring their best selves to work every day and everyone is expected to be treated with respect and professionalism. Employment decisions are based solely on merit, qualifications, performance and capability.

Why Work for Us

At Citizens, you’ll find a customer-centric culture built around helping our customers and giving back to our local communities. When you join our team, you are part of a supportive and collaborative workforce, with access to training and tools to accelerate your potential and maximize your career growth

Background Check

Any offer of employment is conditioned upon the candidate successfully passing a background check, which may include initial credit, motor vehicle record, public record, prior employment verification, and criminal background checks. Results of the background check are individually reviewed based upon legal requirements imposed by our regulators and with consideration of the nature and gravity of the background history and the job offered. Any offer of employment will include further information.