Irregular Warfare Expert

Confidential; United States; Remote; USD 69,000 - 138,000; Part time

Job summary

Zekai is seeking contractors with a background in the US military or allied defense to support AI training and evaluation projects focused on special operations and irregular warfare.

You will apply your operational expertise to assess complex military scenarios, evaluate tactical and strategic reasoning, and contribute to realistic military assessments that improve how AI systems understand mission planning and decision-making.

Qualifications

• Experience in Special Operations Forces or irregular warfare within military/defense org.
• Strong understanding of unconventional warfare and operational planning.
• Experience applying tactical or operational judgment in military environments.

Responsibilities

• Develop realistic, unclassified scenarios involving special operations and irregular warfare.
• Review and assess military-related content for accuracy and realism.
• Evaluate tactical and operational decisions, identify gaps and unsupported assumptions.
• Apply knowledge of special operations doctrine and mission planning.
• Provide structured feedback to support project deliverables.

Skills

SOF experience

Analytical thinking

Written communication

Operational planning

Job description

Role type: Contractor

Location: Remote

Commitment: Flexible, project or task-based

Compensation: Typically $50–$100 USD/hour, negotiable based on experience

Project duration: Dependent on customer requirements

About the opportunity

our partner is looking for experienced Special Operations and Irregular Warfare professionals with backgrounds in the US military, Special Operations Forces (SOF), or allied defense organizations to support customer projects focused on AI training and evaluation.

In this role, you'll apply your operational expertise to assess complex military scenarios, evaluate tactical and strategic reasoning, and contribute to the development of realistic military assessments.

Your expertise will help improve how AI systems understand special operations, unconventional warfare, mission planning, and operational decision-making.

What you'll do

• Develop realistic, unclassified scenarios involving special operations, irregular warfare, and military planning.
• Review and assess military-related content for operational accuracy, relevance, and realism.
• Evaluate tactical and operational decisions, identifying gaps, inconsistencies, and unsupported assumptions.
• Apply professional knowledge of special operations doctrine, mission planning, and operational risk assessment.
• Provide structured feedback and clear explanations to support project deliverables.

Required qualifications

• Professional experience in Special Operations Forces, irregular warfare, or special operations planning within military or defense organizations.
• Strong understanding of unconventional warfare, special operations missions, and operational planning.
• Experience applying tactical or operational judgment in military environments.
• Strong analytical, critical-thinking, and written communication skills.

Preferred qualifications

• Previous experience with USSOCOM, US Army Special Forces, Naval Special Warfare, Marine Raiders, Air Force Special Operations, or comparable allied units.
• Experience in unconventional warfare, counterterrorism, foreign internal defense, or special reconnaissance.
• Background in joint operations, mission planning, intelligence support, or operational risk assessment.
• Experience developing operational assessments, military reports, training materials, or doctrine.
• Experience in deployed operational environments or multinational military operations.

Application process

• Candidates will complete an AI interview as part of the application process.

Learn More About Our Government & Defense Work

At our partner, we work with government and defense experts to evaluate how advanced AI models perform on real-world tasks.

Our MissionReport benchmark assesses AI-generated military and government reports, highlighting the importance of expert judgment, accuracy, and operational understanding.

Learn more: https://www.our partner/benchmark/mission-report

This is a 100% remote contract role, open to applicants worldwide in the countries the employer accepts.