Legal Expert — AI Evaluation & Reasoning
About the Role
A structured AI initiative focused on developing evaluation tasks that measure legal reasoning in complex enterprise environments. The work reflects the regulatory, transactional, compliance, and risk considerations encountered by large public companies.
This opportunity is ideal for experienced legal professionals with substantial enterprise legal experience and expertise in areas such as M&A, securities, regulatory matters, employment, intellectual property, privacy, or commercial contracting. Strong candidates should be able to translate senior-level legal judgment into realistic scenarios and objective evaluation criteria.
The work involves creating enterprise legal scenarios, preparing reference-quality analyses, and developing detailed rubrics that distinguish sound legal reasoning from superficial responses. Accuracy, practical judgment, and precise written analysis are critical.
What You'll Do
- Construct realistic enterprise legal scenarios across in-house, regulatory, transactional, and litigation contexts
- Develop scenarios involving FCPA, SOX, GDPR, HIPAA, and sector-specific regulatory requirements
- Create enterprise contracting tasks involving MSAs, SOWs, DPAs, licensing, and related agreements
- Develop M&A due-diligence scenarios reflecting complex transaction environments
- Build enterprise risk-management and COSO-aligned scenarios
- Create board-level reporting and regulated-industry investigation scenarios
- Draft reference-quality legal analyses and expected solutions
- Author detailed, criterion-based rubrics that evaluate senior-level legal reasoning
- Review and refine evaluation materials to meet established quality standards
- Incorporate calibration and reviewer feedback into subsequent work
Requirements
- Minimum 2 years of experience as in-house counsel at a Fortune 500 or large public company, or as a partner/senior associate at an AmLaw 100 firm representing large enterprise clients
- Deep expertise in at least one enterprise legal practice area, including M&A, securities, regulatory, employment, IP, privacy, or commercial contracting
- JD or equivalent U.S. legal qualification
- Active U.S. bar admission
- Strong written English and precise legal drafting ability
- Ability to translate practical legal judgment into structured evaluation criteria
- Familiarity with enterprise compliance and risk-management frameworks
- Comfortable working remotely and independently on a flexible schedule
- Ability to commit to a minimum of 20 hours per week
- Familiarity with CLM platforms such as Ironclad, Agiloft, or Icertis is preferred
- Familiarity with enterprise GRC tooling is preferred
- Prior experience creating rubrics, examinations, training materials, or evaluation content is preferred
- Must be able to work as an independent contractor and satisfy applicable onboarding and work-authorization requirements
- Access to confidential or proprietary information from current or former employers, clients, or institutions is not required for the work