Red Team Operator
Waukesha, Waukesha County, Wisconsin, 53188, USA
Listed on 2026-06-30
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IT/Tech
Cybersecurity
Team Overview
At Trans Union, this role will report to a Director of Cybersecurity. We are seeking an experienced and highly skilled Red Teamer to join our Information Security Department. The Red Team Leader will primarily be responsible for conducting in-depth threat emulation exercises such as Red Team Operations, Purple Team Operations, and Penetration Tests to assess the security of our systems, networks, and applications.
This is a remote position which may require occasional in‑person attendance at work‑related events at the discretion of management.
- Conduct comprehensive threat emulation exercises, actively simulating cyber‑attacks to uncover vulnerabilities in systems, networks, and applications.
- Collaborate with cross‑functional teams to perform purple team exercises that challenge the organization’s overall security posture.
- Perform lateral movement within target environments to assess the effectiveness of internal network segmentation and access controls.
- Demonstrate expertise in local privilege escalation techniques.
- Emulate threat actors by replicating their techniques, tactics, and procedures to identify vulnerabilities and gaps in our defensive measures.
- Develop and utilize custom scripts, tools, and frameworks to enhance red team operations and mimic real‑world attacks.
- Conduct reconnaissance activities to gather intelligence on potential targets and identify attack vectors.
- Test the security of cloud‑based environments and identify weaknesses in configurations, access controls, and data protection mechanisms.
- Document and communicate findings, risks, and recommendations in clear and concise reports to stakeholders, including technical and non‑technical audiences.
- 5+ years of active experience in conducting penetration tests and actively working as a red teamer; proven track record in performing red team operations and purple team operations.
- Proficiency in the ability to compromise a modern organization, elevate privileges, move laterally through complex networks, and achieve adversary goals.
- Strong experience and expertise in phishing techniques, social engineering tactics, and other initial access methods.
- Extensive experience in writing comprehensive and well‑structured reports detailing findings, risks, and actionable recommendations.
- Basic development experience (Python, Bash, Git, etc.) to create custom solutions for bleeding‑edge problems.
- Industry certifications such as OSCP, OSCE, GPEN, GWAPT, CISSP, or equivalent would be an advantage.
For Your Health:
Enjoy day‑one eligibility for medical, dental, and vision coverage, plus supplemental plan options. Spousal, domestic partner, and other eligible dependent coverage is available on select plans. Choose tax‑advantaged HSA and FSA accounts to make everyday care more affordable.
For Your Protection:
We’ve got your back with company‑paid basic life and AD&D, optional voluntary life and AD&D for you and your family, and short and long‑term disability. You can also opt into a legal plan, pet insurance, and travel accident coverage.
For Your Family:
From adoption assistance and fertility planning coverage to caregiver support, we’re here for every chapter. Access Dependent Care FSA for possibility of an employer match, a complimentary Care@Work membership, and up to 12 weeks of paid parental leave with eligibility for a thoughtful, gradual return.
For Your Future:
Build toward what’s next with our 401(k) with employer match and Employee Stock Purchase Plan (ESPP). Tap financial wellness resources, career coaching, and optional long‑term care insurance to plan confidently.
For You:
Grow and recharge with tuition reimbursement, flexible time off for exempt employees or paid time off for non‑exempt employees, up to 12 paid holidays per year, commuter benefits, employee discounts, charitable gift matching, and paid volunteer time off, plus corporate volunteer events that make it easy to give back.
For Your Wellness:
Access 24/7 support including professional therapy, coaching, and emotional well‑being programs alongside guided meditation and…
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