Military Writing Specialist (Remote AI Evaluation Contract)

Welcome to Jobtacular! We connect top-tier domain practitioners directly with frontier AI labs. We are on the hunt for a sharp, detail-oriented Military Writing Specialist (Remote AI Evaluation Contract) ($40 - $80/hour) to assist with benchmarking and human evaluation. If you have deep experience in military writing, federal documentation standards, report generation and evaluation, grading rubric development, this flexible engagement gives you the freedom to set your own hours while earning top-market hourly rates.

The Role & What You'll Tackle

the partner network is engaging Military Writing Specialists to support a unique project, leveraging expertise in military writing and reporting. In this role, you'll apply your expertise to help train next-generation AI systems. Your work will shape how models learn, reason, and perform through high-quality, real-world input. No prior experience in AI is required — your domain knowledge is what matters. Contributors will use their background in Department of War (Department of Defense) documentation to generate, review, and evaluate a wide range of reports, summaries, and status updates reflective of authentic military processes. Your input will help develop benchmarks and grading guidelines that will teach AI to understand and replicate effective, compliant government communication.

Scope of Work

1. Create realistic military and federal status reports, summaries, and executive updates based on prompts and supplied artifacts.
2. Develop “golden responses” that demonstrate high-quality, standards-aligned reporting for use in AI model training.
3. Draft grading rubrics and guidelines that reflect best practices in federal and military writing assessment.
4. Evaluate AI-generated reports, providing detailed feedback in both written and verbal form.
5. Share context on stylistic differences and individual approaches to common military documents (e.g., WARs, SITREPs, AARs, executive summaries).
6. Produce supporting documents such as decision briefs, memoranda, and action officer updates when required.
7. Collaborate with other subject matter experts to ensure diversity of reporting styles and adherence to branch-specific terminology.

Preferred Qualifications

1. Former U.S. Department of War (Department of Defense) professional with at least 3 years of relevant experience.
2. Experience producing templated and standard reports such as Weekly Activity Reports (WARs), Situation Reports (SITREPs), After-Action Reviews, or similar artifacts.
3. Expertise spanning two or more branches of the U.S. military is a plus; a diverse background across roles is highly valued.
4. Proven proficiency in written and verbal communication, particularly in conveying technical or operational subject matter.
5. Demonstrated ability to craft, grade, and review back office documents, PowerPoints, memos, and spreadsheets for military or federal purposes.
6. US-based contributor with broad familiarity with federal documentation standards and compliance best practices.
7. Comfortable collaborating remotely and sharing insights on nuanced, highly procedural reporting tasks.

Rate, Schedule & Why You'll Love It

This contract position is offered at $40 - $80/hour with immediate onboarding upon approval. Work 100% remotely from the United States, UK, Canada, Australia, New Zealand, or Ireland. Candidates are evaluated on verified subject matter mastery. Select Apply Now below to access the official candidate assessment portal directly.