Irregular Warfare Expert

$50–100/hr

rate as listed

Workload: ~15h/week
Engagement: Project-based
Location: Worldwide
Field: Generalist

Apply special operations and irregular warfare experience to create unclassified scenarios and evaluate AI-generated military reasoning. The work focuses on operational accuracy, mission planning, risk assessment, and clear written feedback.

The work

Contractors develop realistic, unclassified scenarios involving special operations, irregular warfare, and military planning. Day-to-day tasks may include reviewing military content for operational accuracy, assessing tactical or operational decisions, identifying unsupported assumptions, and explaining how doctrine, mission context, intelligence, or risk should affect an assessment.

The screening

The application includes an AI interview. Expect follow-up questions about verifiable military or defense experience, special operations doctrine, unconventional warfare, mission planning, and examples of applying tactical or operational judgment. Strong responses distinguish doctrinal concepts precisely, use sanitized specifics from real work, and show how conclusions were reached without disclosing classified, controlled, or operationally sensitive information.

Logistics

This is a remote contractor role with flexible, project-based or task-based commitments. Project duration depends on customer requirements, while typical weekly hours and whether all work is asynchronous are not specified.

Pay band: $50–100/hr

What they look for

special operations doctrine
operational planning
tactical and operational judgment
analytical skills
written communication
scenario development
unconventional warfare
operational risk assessment
military report writing
critical thinking

Included with this listing

Interview prep — 10 questions

Matched to what this platform's screening actually measures. Answer each out loud in 60–90 seconds: claim → concrete example → implication.

What it tests: This establishes whether your experience came from direct operational, planning, intelligence, training, or assessment responsibilities and whether the scope can be verified under follow-up.
A strong answer: Give role titles, organization types, approximate timeframes, level of responsibility, and the kinds of decisions or products you owned. Keep examples sanitized and explicitly separate direct experience from adjacent support.
Where people lose it: Candidates lose points by relying on unit affiliation or broad claims while never identifying what they personally planned, assessed, decided, or produced.

Summary, eligibility guidance and screening preparation are prepared by Sidequest from the platform's posting. Check the source listing before applying.