Sr. Info Security Specialist

Cboe Global Markets•Chicago, IL

2d•Hybrid

About The Position

The Security Operations team is hiring a Senior Red Team Specialist. 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 real‑world adversaries and rigorously test enterprise security controls. This role is deeply technical and hands‑on, 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 enterprise‑wide 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.

Requirements

5+ years of experience in red teaming, penetration testing, or offensive security, with demonstrated hands‑on impact
Bachelor’s degree or equivalent practical experience
Strong knowledge of attacker tradecraft and TTPs across modern enterprise environments
Hands‑on 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 experience operating within defined rules of engagement
Candidates must be legally authorized to work in the United States without the need for employer sponsorship now or in the future.

Nice To Haves

Experience executing threat‑intelligence‑informed adversary emulation, not just vulnerability‑driven testing
A track record of 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
Experience operating in regulated or large enterprise environments
Demonstrated ability to mentor junior analysts or contribute to internal training materials
Curiosity, adaptability, and a continuous improvement mindset

Responsibilities

Executing adversary emulation and red team engagements aligned to real‑world threat actor techniques and objectives
Performing hands‑on offensive operations, including initial access, persistence, privilege escalation, lateral movement, and command‑and‑control
Developing, maintaining, and safely using custom red team tooling, scripts, and techniques
Working closely with detection and threat hunting teams to validate detections and response effectiveness during red and purple team exercises
Assisting in the design and execution of assumed breach scenarios and multi‑stage attack chains
Identifying control gaps, detection blind spots, and architectural weaknesses across enterprise environments
Supporting incident response teams during complex investigations by providing attacker 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

Benefits

Fair and competitive salary and incentive compensation packages with an upside for overachievement
Generous paid time off, including vacation, personal days, sick days and annual community service days
Health, dental and vision benefits, including access to telemedicine and mental health services
2:1 401(k) match, up to 8% match immediately upon hire
Discounted Employee Stock Purchase Plan
Tax Savings Accounts for health, dependent and transportation
Employee referral bonus program
Volunteer opportunities to help you give back to your communities
Complimentary lunch, snacks and coffee in any Cboe office
Paid Tuition assistance and education opportunities
Generous charitable giving company match
Paid parental leave and fertility benefits
On-site gyms and discounts to other fitness centers