Contracting Attorney

About this role

Job Summary: In this role, you'll apply your expertise to help train next-generation AI systems. Your work will shape how models learn, reason, and perform through high-quality, real-world input. No prior experience in AI is required — your domain knowledge is what matters. This fellowship simulates real-world contract negotiation scenarios used to train advanced AI models. Fellows will: • Perform simulated contract negotiations and redlining exercises, evaluating AI-generated suggestions for accuracy, risk identification, and legal soundness. • Review and assess AI responses to contract scenarios, providing expert feedback to improve model performance and output precision. • Collaborate with Crosby's product and research teams to refine training data, annotation guidelines, and best practices for AI-driven contract review solutions.

Skills

Required skills & qualifications

• J.D. from an ABA-accredited law school.
• Active bar admission in at least one U.S. jurisdiction.
• Minimum of 3 years of in-house experience focused on technology transactions, particularly SaaS contract review, negotiation, and redlining.
• Exceptional written and verbal communication skills with meticulous attention to detail.
• Strong analytical capabilities and ability to translate legal expertise into actionable feedback for AI systems.
• Demonstrated commitment to innovation at the intersection of law and technology.
• Experience working with cross-disciplinary teams in fast-paced environments.

Preferred qualifications

• Prior exposure to AI, legal tech, or data annotation initiatives.
• Expertise in risk mitigation strategies within SaaS contracting.
• Publication or presentation record on legal technology topics.
• Applications will be reviewed on a rolling basis, and the fellowship will close once the cohort is full. Apply by April 30 for the best chance of securing a spot.