Intermediate Red Team Operator

Watershed Security
Norfolk, VA

Watershed Security, is a Veteran Owned Small Business with over 20 years’ Cybersecurity and Government Contracting experience. Watershed is looking for an Intermediate Red Team Operator to support U.S. Navy acquisition and operational programs. This position supports cyber Operational Test and Evaluation (OT&E) activities across a diverse set of Navy platforms, weapon systems, information warfare capabilities, and enterprise business systems. The Operator will assist in the development of cyber OT&E test plans, execute authorized cyber testing activities, and produce detailed reports documenting test results and findings. Testing will be conducted across live operational environments, laboratories, cyber ranges, and cloud-based services, encompassing both information technology (IT) and operational technology (OT) systems. System safety and operational security are critical priorities in all test environments. The role involves leveraging approved tools, resources, and analytic techniques to penetrate and access systems and networks under test in support of mission objectives. The Operator will perform testing under the direction of the OID Current Operations Officer and apply established red team tradecraft in accordance with defined rules of engagement, onsite at Norfolk, VA.

REQUIRED QUALIFICATIONS

An Intermediate Red Team Operator must meet all qualification requirements of a Basic Red Team Operator plus:
  • Proficient in at least two operating systems (Windows, Linux, or Unix variants)
  • Proficient in at least one offensive tool: Metasploit, Cobalt Strike, or Core Impact
  • Able to independently conduct penetration testing/red teaming under guidance
  • Able to independently generate red team report documents
  • Certified Ethical Hacker Certification or equivalent
  • Certification Required to start Offensive Security Certified Professional (OSCP) or equivalent
  • Must have active TS with SCI Eligibility
  • Minium of 3 years in any combination of penetration testing, red teaming, or exploitation development
  • Demonstrated proficiency with offensive tools: Metasploit, Cobalt Strike, Core Impact, Burp Suite, Nessus, and SharpHound
  • Demonstrated Technical and Analytical Skills needed:
    • Detect malicious activity using dynamic analysis techniques
    • Independently conduct penetration testing/red teaming to accomplish assigned objectives
    • Ability to identify and analyze malicious program behavior using dynamic analysis techniques
    • Proven experience to independently plan and execute penetration testing and red team activities to successfully meet assigned test objectives
    • Solid understanding of Windows and Unix/Linux system internals, host-based security products, and how configurations and protections affect exploitation and detection
  • Work is onsite Norfolk, VA Monday – Friday 8am -4.30pm EST
  • Possibility of travel up to 10%
DESIRED QUALIFICATIONS
  • Experience in DOD preferably Navy Operational Test and Evaluation (OT&E) environments
  • Proficient with MS Office Suite
  • Strong written and verbal communications
*Contingent upon award*
PAY RANGE
Final salary is influenced by factors such as location, contract labor categories, experience, skills, education, and certifications. Watershed offers competitive compensation, medical and dental benefits, educational reimbursement, 401K plans with matching, 15 days of PTO to start and 11 paid holidays per year. The proposed salary range for this position is: $80,000.00 - $92,700.00 USD.

Equal Opportunity Employer / Individuals with Disabilities / Protected Veterans

Posted 2026-02-21

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