Saas Contracting Attorney - AI Fellowship

Job Type: Contractor

Location: Remote

Job Summary:

We''ve partnered with Crosby to find seasoned commercial attorneys for a 1-month Commercial Contracting AI Fellowship. This opportunity is for elite lawyers who want to help shape how advanced AI is trained, evaluated, and applied in real-world legal work — especially those with deep experience in SaaS contract review, negotiation, and redlining. As a SaaS Contracting Attorney – AI Fellow, your contributions will directly refine and elevate next-generation legal AI systems, driving meaningful change in the industry.

This fellowship simulates real-world contract negotiation scenarios used to train advanced AI models. Fellows will:

1. Perform simulated contract negotiations and redlining exercises, evaluating AI-generated suggestions for accuracy, risk identification, and legal soundness.
2. Review and assess AI responses to contract scenarios, providing expert feedback to improve model performance and output precision.
3. Collaborate with Crosby''s product and research teams to refine training data, annotation guidelines, and best practices for AI-driven contract review solutions.

Required Skills and Qualifications:

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

Compensation and commitment

1. $80–$105/hour
2. Part-time, flexible schedule
3. Minimum commitment: 5 hours/week
4. Maximum commitment: 20 hours/week
5. Fellowship duration: 1 month

Preferred Qualifications:

1. Prior exposure to AI, legal tech, or data annotation initiatives.
2. Expertise in risk mitigation strategies within SaaS contracting.
3. 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.