Legal Specialist, Contract Engagement

About Fleet AI

Fleet AI builds training environments where AI agents practice real tasks and their work can be evaluated. Our legal projects use realistic matters and legal work products to evaluate how well those agents research, reason, and support their conclusions.

Scope of services

Develop legal tasks and reference materials for AI training and evaluation. Each engagement will specify the practice area, jurisdiction, outputs, and acceptance criteria.

Deliverables

Each project will specify the outputs to be delivered. These may include:

• A legal assignment with a case file and supporting documents.
• A reference memo, brief, diligence report, or other work product that answers the assignment.
• Evaluation criteria grounded in the case file and relevant legal authorities.
• Reviews of AI-generated work identifying errors in legal reasoning, factual support, citations, or conclusions.

We are interested in prior work demonstrating

• Experience in US legal practice, ideally as a senior paralegal or attorney, with substantive research, drafting, or document review experience. Active bar admission is a plus but not required.
• Ability to explain why a conclusion is supported, where the evidence is incomplete, and why an error matters.
• Clear written analysis grounded in the relevant facts and jurisdiction.

Engagement structure

• Format: Remote, part-time contract.
• Initial term: The first phase runs through October 31, 2026, as part of a multi-phase, long-term program.
• Location: United States only. Fleet is unable to sponsor work authorization in the United States or elsewhere.
• Terms: Scope, deliverables, fees, and an end date are agreed before work begins, and any extension is agreed in writing. A Fleet project contact handles scoping questions and reviews submitted deliverables.

Fees

• Rate: $150–$200 USD per hour.
• Increases and bonuses: Top performers may earn higher rates based on quality, consistency, and throughput. Per-task bonuses may be available for especially challenging, high-quality work.
• Tools: Reasonable AI tool subscriptions are reimbursed.

Express Interest

Apply using the form on this page. The selection process is a short, unpaid online assessment in which you review a legal task. There is no interview. Instructions and expected completion time are provided before you start.

Referrals: $500 once someone you refer completes 40 hours of work.

Where you can work

This role is 100% remote, for applicants located in United States.