Red Teaming Jobs in Boston, MA (NOW HIRING)

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 & Work Arrangement: Remote is not an option, candidates must be willing to commute to one of the following hub locations with a hybrid schedule of 4 days onsite and 1 day remote per week with flexibility in one of the following hubs:

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

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.

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 - https://jobs.citizensbank.com/benefits.

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