Sr. Red Team Specialist

Cedar Cares, Inc; Chicago (IL); On-site; USD 121,550 - 157,300; Full time

Benefits offered by this job

Generous paid time off

Health, dental, and vision benefits

401(k) match

Paid tuition assistance

Job summary

Cedar Cares, Inc is looking for a Senior Red Team Specialist to execute advanced offensive security operations and engage in hands-on security engagements. Applicants should have over 5 years of experience in red teaming and strong communication skills. This role follows a hybrid work model, focusing on enhancing enterprise security through emulation of real-world threats.

The position offers competitive compensation, benefits including health plans, generous paid time off, and opportunities for professional development.

Qualifications

• 5+ years of experience in red teaming, penetration testing, or offensive security.
• Strong knowledge of attacker tradecraft and TTPs across modern enterprise environments.
• Hands-on experience in endpoint, identity, cloud, and hybrid infrastructures.

Responsibilities

• Executing adversary emulation and red team engagements.
• Performing hands-on offensive operations like persistence and privilege escalation.
• Producing clear, actionable reporting for technical findings.

Skills

Red teaming experience

Offensive security knowledge

Ethics and engagement standards

Written and verbal communication

Education

Bachelor’s degree or equivalent experience

Tools

Python

PowerShell

Bash

Job description

About the Role

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. It 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. This role follows a four‑day in‑office work model.

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

Qualifications

• 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

Preferred Skills

• Experience executing threat‑intelligence‑informed adversary emulation, not just vulnerability‑driven testing
• 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

Benefits and Perks

• Fair and competitive salary and incentive compensation packages with 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

Salary

At Cboe, we are committed to providing a competitive, transparent, and market‑informed total rewards program. The anticipated base salary range for this role is $121,550–$157,300, with actual compensation determined by job‑related factors such as skills, relevant experience, education, internal alignment, and location. This role may also be eligible for annual incentive compensation and, where applicable, participation in Cboe's long‑term equity programs.

Visa Sponsorship

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.

Equal Employment Opportunity

We’re proud to be an equal opportunity employer and do not discriminate against any employee or applicant for employment based on any legally protected characteristic, including race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, genetic information, or veteran status. We are committed to fostering a workplace where all individuals are valued and respected.