About The Position

This role sits within a specialized enterprise security organization focused on protecting sensitive data across complex global environments. The team works at the intersection of cybersecurity, insider risk, and data protection, collaborating with engineering, governance, and risk teams to evolve security controls and detection strategies. The environment is fast-paced, collaborative, and technical, with an emphasis on proactive threat simulation and continuous improvement. The Senior Red Team Analyst designs and executes simulations focused on insider threats and data exfiltration, tests enterprise Data Loss Prevention (DLP) controls, identifies gaps and bypass techniques, and works with engineering teams to improve detection and enforcement. The role also reports findings and remediation strategies to stakeholders and validates remediation through continued testing. Engagement is W2 only; C2C and 1099 arrangements are not accepted.

Requirements

  • At least 5 years of experience in red team, offensive security, or adversary simulation roles.
  • Hands-on experience testing or bypassing DLP controls.
  • Strong knowledge of insider threat behaviors and data exfiltration techniques.
  • Experience with endpoint, email, cloud, and collaboration security environments.
  • Direct experience with Microsoft Purview (DLP, Insider Risk), Varonis, and Proofpoint (TAP/TRAP/CASB).
  • Familiarity with unstructured data environments and user-driven data movement risks.
  • Ability to translate technical findings into business- and risk-focused insights.
  • Strong communication skills and ability to present to leadership and cross-functional teams.

Nice To Haves

  • Experience in regulated industries such as financial services, healthcare, or technology.

Responsibilities

  • Design and execute red team simulations focused on insider threat and data exfiltration scenarios.
  • Test and challenge DLP controls across endpoints, email, cloud platforms, and collaboration tools.
  • Identify control gaps, bypass techniques, and misconfigurations in enterprise data protection frameworks.
  • Partner with engineering teams to refine detection logic, policies, and enforcement mechanisms.
  • Simulate high-risk user behaviors, including privileged access misuse, third-party risk, and employee offboarding scenarios.
  • Deliver reports outlining vulnerabilities, risk exposure, and remediation strategies.
  • Present findings to senior stakeholders and contribute to enterprise-level security decisions.
  • Validate remediation efforts through continuous testing and reassessment.

Benefits

  • Opportunity to work on cutting-edge insider threat and data protection initiatives.
  • Exposure to advanced enterprise security tools and real-world adversary simulation scenarios.
  • High-impact role influencing enterprise-wide security posture and risk mitigation strategies.
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