Red Team Analyst - Data Loss Prevention (Enterprise Information Protection) (1150)

Contract · Poss. to Hire

Hybrid · Charlotte, NC

W2 Only · No 3rd Parties

Experience

Serve as an offensive security specialist within the Enterprise Information Protection (EIP) program, responsible for testing, validating, and stress-testing DLP controls against real-world insider threat and data exfiltration scenarios. This role thinks like a malicious insider - employee, contractor, or compromised identity - to simulate data loss techniques across endpoints, email, cloud collaboration platforms, and unstructured data repositories. Findings directly inform control improvements, detection tuning, policy enforcement, and insider risk modeling.

Responsibilities

1. Design and execute red team-style data exfiltration scenarios aligned to insider threat, negligent user, and compromised account risk.

2. Simulate data loss techniques across endpoint, email, cloud storage, collaboration tools, web upload, printing, and removable media.

3. Test DLP controls for bypass techniques, misconfigurations, policy gaps, and detection blind spots.

4. Emulate high-risk behaviors tied to role-based access, privileged users, leavers, and third-party identities.

5. Validate effectiveness of DLP policies, sensitivity labels, endpoint controls, and alerting logic.

6. Partner with EIP engineering teams to tune detection rules, thresholds, and policy guardrails.

7. Execute testing tied to new DLP capabilities, roadmap initiatives, and tool deployments such as endpoint DLP and unstructured data controls.

8. Produce clear, defensible reports outlining attack paths, control weaknesses, risk severity, and remediation guidance.

9. Present findings to EIP leadership, Insider Risk governance forums, and control owners.

10. Track remediation activities and validate improvements through retesting.

Required Tools & Platforms

Microsoft Purview Varonis Proofpoint TRAP Proofpoint TAP Proofpoint CASB

Skills & Experience

Core Technical Skills

Red Team / Adversary Simulation DLP Bypass Techniques Data Exfiltration Testing Endpoint Security Controls Email Security Cloud Security (CASB) Sensitivity Labels Unstructured Data Environments Purple Team Operations Detection Tuning Policy Gap Analysis Threat Modeling

Insider Risk & Domain

Insider Threat Programs Privileged User Emulation Leaver / Joiner Risk 3rd-Party Identity Risk Human-Centric Threat Modeling Insider Risk Governance

Industry Background

Financial Services Healthcare Technology / Regulated Env.

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