Junior Transactional Attorney

Weekday AI
•$70 - $90•Remote

About The Position

This part-time contractor role is for a client and is remote. It is intended for an early-career lawyer with foundational transactional legal experience, particularly in drafting, reviewing, and redlining contracts in technology or corporate settings. The attorney will apply practical legal judgment to help train and evaluate AI systems for contract review and negotiation. Work includes assessing AI-generated responses to legal scenarios, conducting simulated contract negotiations, and providing structured feedback to improve the accuracy, consistency, and quality of AI-driven legal solutions. The role involves collaboration with legal, product, engineering, and research teams.

Requirements

  • 1–3 years of transactional legal experience at a law firm or within an in-house legal team.
  • Foundational experience drafting, reviewing, negotiating, and redlining commercial agreements.
  • Familiarity with Master Services Agreements (MSAs), Non-Disclosure Agreements (NDAs), and other commercial contracts.
  • Strong understanding of contractual provisions, legal terminology, risk allocation, and negotiation principles.
  • Excellent written and verbal communication skills and exceptional attention to detail.
  • Strong analytical and critical-thinking abilities, including explaining legal reasoning and translating it into actionable feedback.
  • Interest in legal technology, artificial intelligence, and applying AI to transactional legal workflows.
  • Ability to work independently and collaborate effectively with cross-functional teams in a dynamic environment.

Nice To Haves

  • Previous exposure to legal AI products, legal technology platforms, or AI training and evaluation initiatives.
  • Internship or professional experience at a corporate law firm.
  • Exposure to M&A transactions, fund formation, or other complex corporate legal matters.
  • Experience evaluating legal documents against structured criteria or established review guidelines.
  • Experience with legal AI and legal technology, AI model evaluation and training, corporate law firm work, mergers and acquisitions, fund formation, contract negotiation, legal data annotation and quality assessment, or technology-sector agreements.

Responsibilities

  • Perform simulated contract negotiations, review contractual language, and redline documents to identify risks and recommend revisions.
  • Evaluate AI-generated responses to contract-related scenarios for legal accuracy, relevance, completeness, and practical applicability.
  • Apply evaluation frameworks, grading rubrics, and assessment criteria to AI performance on transactional legal tasks.
  • Identify contractual risks, ambiguous provisions, unfavorable terms, and potential compliance concerns, and provide recommendations.
  • Provide structured, actionable feedback to improve AI models' understanding of contractual language, legal reasoning, and negotiation strategies.
  • Collaborate with product, engineering, and research teams to refine datasets, evaluation guidelines, and best practices for AI-powered contract review.
  • Ensure evaluations are objective, detailed, and consistent with legal standards and task-specific guidelines.

Benefits

  • Flexible part-time engagement and professional schedule flexibility.
  • Opportunity to develop expertise in legal AI evaluation, contract analysis, and technology-enabled legal workflows.
  • Opportunity to collaborate with legal, product, and research professionals.
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