AI Legal Advisor & Quality Evaluator

Obsidian; Chicago (IL); On-site; USD 83,000 - 165,000; Part time

Job summary

Obsidian in Chicago seeks an experienced Lawyer to help evaluate and improve AI systems. You will assess AI-generated legal content and workflows, applying real-world litigation, drafting, and client advisory expertise.

The role requires 4+ years in legal practice, ability to work 20+ hours weekly, and strong English writing. Start immediately; project spans about 4-6 weeks with task-based pay upfront and potential hourly follow-on.

Qualifications

• 4+ years of legal practice as a Lawyer or related role.
• Experience in criminal and/or civil proceedings.
• Willing to commit 20+ hours per week.
• Strong written English communication.

Responsibilities

• Evaluate AI-generated legal memoranda, contracts, and analyses for quality and accuracy.
• Compare AI-generated responses based on legal reasoning and drafting rigor.
• Provide expert feedback on litigation strategy, statutory interpretation, and client advisory decisions.

Skills

Legal experience 4+ years

Litigation experience

Drafting & advisory

English writing

Job description

Obsidian in Chicago seeks an experienced Lawyer to help evaluate and improve AI systems. You will assess AI-generated legal content and workflows, applying real-world litigation, drafting, and client advisory expertise.

The role requires 4+ years in legal practice, ability to work 20+ hours weekly, and strong English writing. Start immediately; project spans about 4-6 weeks with task-based pay upfront and potential hourly follow-on.