Legal Expert – AI Evaluation & Enterprise Law

About the role

We are seeking experienced legal professionals to help develop high-quality evaluation tasks for AI systems operating in complex Fortune 500 and large public-company legal environments. In this role, you’ll create realistic enterprise legal scenarios, develop reference-quality work products, and build detailed evaluation rubrics that distinguish strong legal reasoning from superficial or incomplete responses. The work reflects the regulatory complexity, transaction scale, and risk considerations faced by large enterprises.

Responsibilities

• Develop realistic legal scenarios covering in-house counsel, regulatory, transactional, and litigation matters for Fortune 500‑scale organizations.
• Create and review materials involving major enterprise compliance frameworks, including FCPA, SOX, GDPR, HIPAA, and industry‑specific regulations across banking, healthcare, pharmaceuticals, and insurance.
• Design tasks involving large‑scale commercial agreements such as MSAs, SOWs, DPAs, and licensing agreements, as well as M&A due diligence.
• Develop enterprise risk management (ERM) and COSO‑aligned scenarios, board‑level reporting exercises, and investigations involving regulated industries.
• Create detailed, criterion‑based rubrics that reflect the professional judgment expected from senior legal counsel at large public companies.
• Help establish consistent quality standards for evaluating AI‑generated legal work.

Qualifications

Ideal candidates will have:

• 2+ years of experience as in‑house counsel at a Fortune 500 or large public company, or experience as a partner/senior associate at an AmLaw 100 firm representing Fortune 500 clients.
• Strong experience in one or more enterprise legal practice areas, such as M&A, securities, regulatory law, employment law, intellectual property, privacy, or commercial contracting.
• Experience working with enterprise legal technology, including CLM platforms such as Ironclad, Agiloft, or Icertis, is beneficial.
• Familiarity with enterprise GRC (Governance, Risk, and Compliance) tools is a plus.
• JD degree with active bar admission required.
• Previous experience creating legal rubrics, examinations, training materials, or professional evaluation content is an advantage.

Compensation & Commitment

Hourly compensation: $110–$150 per hour, based on demonstrated expertise. Minimum commitment: 20 hours per week. Onboarding includes a paid training and calibration program designed to familiarize contributors with the required quality standards. High‑performing contributors may have opportunities to progress into reviewer, lead, and domain subject‑matter expert roles, potentially at higher rates.

Engagement is structured as an independent contractor position. Fully remote, with flexibility to complete work according to your own schedule. Project duration may vary depending on business requirements and performance. Work will not require access to confidential or proprietary information belonging to any employer, client, or institution. Payments are made weekly through Stripe or Wise based on completed services.