Red Team Operator (Cybersecurity)

Location: Remote, with occasional in-person attendance at work-related events; role based in Chicago, Illinois, United States

Salary: $112,500–$187,500 annually, with potential eligibility for an annual bonus and, for certain positions, long-term incentives.

Company

hirify.global is a global organization focused on pioneering products, technology, and positive impact for customers and communities.

What you will do

• Conduct threat emulation, red team, purple team, and penetration testing exercises against systems, networks, applications, and cloud environments.
• Simulate real-world threat actors by applying reconnaissance, phishing, social engineering, privilege escalation, lateral movement, and other attack techniques.
• Assess internal network segmentation, access controls, cloud configurations, and data protection mechanisms.
• Develop and use custom scripts, tools, and frameworks to support red team operations and address complex security problems.
• Document vulnerabilities, risks, and recommendations in clear reports for technical and non-technical stakeholders.
• Collaborate with cross-functional teams to evaluate and improve the organization’s security posture.

Requirements

• 5+ years of active experience conducting penetration tests and red team operations, including purple team exercises.
• Ability to compromise modern organizations, escalate privileges, move laterally through complex networks, and achieve adversary objectives.
• Strong expertise in phishing, social engineering, and other initial access methods.
• Experience writing comprehensive, well-structured reports with actionable recommendations.
• Basic development experience with Python, Bash, Git, or comparable tools for creating custom solutions.

Nice to have

• OSCP, OSCE, GPEN, GWAPT, CISSP, or equivalent industry certification.

Culture & Benefits

• Remote work with occasional attendance at work-related events.
• Medical, dental, and vision coverage available from day one, with HSA and FSA options.
• Life, disability, legal, pet insurance, and travel accident coverage options.
• Adoption, fertility, caregiver, dependent care, and up to 12 weeks of paid parental leave support.
• 401(k) with employer match, ESPP, tuition reimbursement, career coaching, flexible or paid time off, and paid holidays.
• Wellness support including therapy, coaching, meditation, and physical, mental, social, and financial well-being resources.