Jobs Companies Weekday AI Applied Legal Benchmark Specialist

About this Applied Legal Benchmark Specialist role at Weekday AI

Weekday AI · Remote · United States

This role is for one of our clients

Compensation: $83-$105 per hour

We are seeking experienced legal professionals to author and review high-quality academic assessment content for an AI research initiative. In this role, you will contribute your legal expertise to the development of rigorous evaluation benchmarks designed to assess how effectively AI systems understand and reason about complex legal concepts.

You may contribute through one of two task types:

Question Authoring: Create original, challenging multiple-choice questions within your area of legal expertise, assess their difficulty, and submit them for quality review.

Question Verification: Review existing questions for legal accuracy, clarity, completeness, and rigor. Make necessary edits, evaluate difficulty, and document the reasoning behind any changes.

Requirements

Law Domains Covered

Opportunities span a broad range of legal specialties, including:

  • Intellectual Property, Privacy & Technology
  • Regulatory & Government Affairs
  • Securities & Capital Markets
  • Financial Regulation & Compliance
  • Private Equity
  • M&A & Transaction Structuring
  • Antitrust, Merger Control & Competition
  • Healthcare, Life Sciences & Pharmaceuticals
  • Environmental, Energy & ESG/Climate Law

Key Responsibilities

  • Develop original legal questions that assess deep conceptual understanding, analytical ability, and legal reasoning rather than surface-level recall.
  • Ensure every question is clear, unambiguous, self-contained, and sufficiently detailed to support a definitive answer.
  • Classify questions by difficulty level: Medium (introductory undergraduate), Hard (advanced undergraduate), or Expert (postgraduate level and above).
  • Provide one correct answer along with nine plausible but subtly incorrect alternatives designed to challenge advanced legal reasoning.
  • Develop concise, logically structured solution explanations that demonstrate the appropriate legal reasoning process.
  • Provide 1–5 credible academic or professional references for each question, drawing from reputable legal publications, academic sources, case law, statutes, and legal repositories.
  • For verification assignments, identify issues involving legal accuracy, clarity, completeness, precision, or solvability and clearly explain any recommended revisions.
  • Apply consistent quality standards across questions and contribute to the development of reliable, gold-standard legal evaluation benchmarks.

Ideal Qualifications

  • JD, LLM, SJD, or doctoral-level qualification in Law or a closely related discipline.
  • Master's-level candidates may be considered where they demonstrate exceptional expertise in a specialized legal domain.
  • Strong command of legal reasoning, statutory and regulatory interpretation, case analysis, and legal research.
  • Deep expertise in at least one of the covered practice areas.
  • Experience with legal education, bar examination content development, academic assessment, judicial clerkships, legal research, or legal writing is highly valued.
  • Excellent written English with the ability to communicate complex legal concepts clearly, precisely, and concisely.
  • Strong attention to detail and the ability to identify subtle legal inaccuracies or ambiguities.
  • Prior experience with AI evaluation, training data, benchmarking, or human-in-the-loop research is a plus.

Opportunity Details

  • Commitment: 10+ hours per week
  • Work Arrangement: Fully remote
  • Work Style: Asynchronous and flexible
  • Engagement: Project-based opportunities with potential for continued participation based on performance and project requirements

Application Process

Interested candidates can submit a resume or relevant professional background highlighting their legal specialization and experience. Selected applicants may be asked to complete a short sample assessment or provide additional information about their subject-matter expertise.

Equal Opportunity

We consider all qualified applicants without regard to legally protected characteristics and provide reasonable accommodations upon request.

Contract & Payment Terms

  • You will be engaged as an independent contractor.
  • The role is fully remote and can be completed on a flexible schedule.
  • Projects may be extended, shortened, or concluded based on project requirements and performance.
  • Work will not require access to confidential or proprietary information belonging to any current or former employer, client, or institution.
  • Payments are made weekly based on services rendered through available payment methods.
  • H-1B and STEM OPT candidates are not eligible for this opportunity at this time.
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About Weekday AI

At Weekday (backed by YC; also Product Hunt #1 product of the day), we are building the next frontier in hiring. We have built the largest database of white collar talent in India and have built outreach tools on top of it to generate highest response rates.

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