Adversary Emulation Jobs in Chicago, IL (NOW HIRING)

TheSecurity Operationsteam ishiringaSenior Red TeamSpecialist.

The Senior Red Team Specialist is a highly skilled individual contributor within the Security Operations organization, responsible for planning and executing advanced offensive security operations that emulate realworld adversaries and rigorously test enterprise security controls. This role is deeply technical and handson, with active engagement across endpoint, identity, cloud, SaaS, network, and application environments.

This position partners closely with Detection Engineering, Threat Hunting, Incident Response, and Purple Team functions to ensure red team engagements drive measurable improvements in detection coverage, response effectiveness, and overall defensive posture. While the role does not own enterprisewide red team strategy, it plays a key role in shaping red team tactics, tooling, and execution standards, and in translating offensive findings into actionable defensive outcomes.

• Executing adversary emulation and red team engagements aligned to realworldthreat actortechniques and objectives

• Performing handson offensive operations, including initial access, persistence, privilege escalation, lateral movement, and commandandcontrol

• Developing,maintaining, and safely using custom red team tooling, scripts, and techniques

• Working closely with detection and threat hunting teams tovalidatedetections and response effectiveness during red and purple team exercises

• Assistingin the design and execution of assumed breach scenarios and multistage attack chains

• Identifyingcontrol gaps, detection blind spots, and architectural weaknesses across enterprise environments

• Supporting incident response teams during complex investigations byprovidingattacker tradecraft insight

• Producing clear, actionable reporting that translates technical findings into operationally relevant recommendations

• Contributing to the improvement of red team processes, safety controls, and engagement playbooks

• Mentoring junior analysts and contributing to skills development across the security operations team

• 5+ years of experience in red teaming, penetration testing, or offensive security,withdemonstratedhandson impact

• Bachelor's degree or equivalent practical experience

• Strong knowledge of attacker tradecraft and TTPs across modern enterprise environments

• Handson experience attacking and evading controls in endpoint, identity, cloud, and hybrid infrastructures

• Working understanding of defensive security technologies, such as EDR, SIEM, identity protection, and cloud security controls

• Experience collaborating in purple team exercises and adapting techniques based on detection feedback

• Ability to independently plan and execute offensive tasks within a defined engagement scope

• Strong written and verbal communication skills, including technical documentation and reporting

• High ethical standards and experienceoperatingwithin defined rules of engagement

• Experience executing threatintelligenceinformed adversary emulation, not just vulnerabilitydriven testing

• A track recordof helping convert red team findings into improved detections or response playbooks

• Strong scripting or automation skills (e.g., Python, PowerShell, Bash) to support tooling and operations

• Familiarity with MITRE ATT&CK for mapping activity and communicating impact

• Experienceoperatingin regulated or large enterprise environments

• Demonstrated ability to mentor junior analysts or contribute to internal training materials

• Curiosity, adaptability, and a continuous improvement mindset

This position is not eligible for visa sponsorship. Candidates must be legally authorized to work in the United States without the need for employer sponsorship now or in the future.

Salary Ranges (applicable for US locations only)

This role may also be eligible for annual incentive compensation and, where applicable, participation in Cboe's long-term equity programs.

Additional information about Cboe's total rewards program, including benefits and other compensation components, can be found here: Total Rewards at CBOE.

Any communication from Cboe regarding this position will only come from a Cboe recruiter who has a @cboe.com email or via LinkedIn Recruiter. Cboe does not use any other third party communication tools for recruiting purposes.