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This job expired on 19/09/2026. It no longer accepts applications.
Transactional Attorney (Remote Contractor)
Weekday AI (YC W21)
Job description
About the role
We are looking for an experienced Transactional Attorney to join a cutting‑edge legal AI project on a part‑time, remote basis. The role is ideal for in‑house lawyers who want to apply their expertise in technology transactions to train and evaluate advanced AI systems that assist with contract analysis and negotiation.
Key responsibilities
- Perform simulated contract negotiations and redlining exercises across a variety of commercial technology agreements.
- Review AI‑generated responses to contract scenarios and provide detailed legal feedback to improve model accuracy.
- Develop evaluation criteria, scoring rubrics, and quality standards for AI performance on drafting and negotiation tasks.
- Collaborate with product, research, and engineering teams to refine training data, legal guidelines, and best practices.
- Identify contractual risks, ambiguities, and negotiation strategies within complex agreements.
- Contribute subject‑matter expertise to enhance AI tools for legal research, contract review, and transactional analysis.
Required profile
- Juris Doctor (J.D.) from an ABA‑accredited law school.
- Active bar membership in at least one U.S. jurisdiction.
- Minimum three years of in‑house experience focused on technology transactions.
- Extensive experience drafting, negotiating, reviewing, and redlining MSAs, NDAs, DPAs, and similar commercial agreements.
- Excellent written and verbal communication with strong attention to detail.
- Analytical mindset capable of translating legal expertise into structured feedback.
- Interest in legal innovation and emerging technologies.
Required skills
- Drafting, negotiating, reviewing and redlining commercial technology agreements.
- Legal analysis of AI‑generated contract responses.
- Developing evaluation rubrics and quality standards for AI performance.
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Weekday AI (YC W21)
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