[Hiring] Transactional Attorney @Weekday AI

Role Description

We are seeking experienced Transactional Attorneys for a part-time opportunity at the forefront of legal AI innovation. This role is ideal for accomplished in-house legal professionals who are passionate about shaping the future of AI-powered legal solutions. Leveraging your expertise in drafting, reviewing, negotiating, and redlining commercial technology agreements, you will help train and evaluate advanced AI systems used in real-world legal workflows.

Your contributions will directly improve how AI models identify contractual risks, interpret legal language, and provide accurate, context-aware recommendations for contract analysis and negotiation.

Key Responsibilities

• Perform simulated contract negotiations and redlining exercises across a variety of commercial agreements.
• Review and evaluate AI-generated responses to contract-related scenarios, providing detailed legal feedback to improve model accuracy and reasoning.
• Develop objective evaluation criteria, scoring rubrics, and quality standards for assessing AI performance on contract drafting and negotiation tasks.
• Collaborate with multidisciplinary product, research, and engineering teams to refine AI training data, legal guidelines, and best practices for contract review workflows.
• Apply practical legal judgment to identify contractual risks, ambiguities, and negotiation strategies within complex commercial agreements.
• Contribute subject matter expertise to improve AI systems designed for legal research, contract review, and transactional analysis.

Qualifications

• Juris Doctor (J.D.) from an ABA-accredited law school.
• Active bar membership in at least one U.S. jurisdiction.
• Minimum 3 years of in-house legal experience focused on technology transactions.
• Extensive experience drafting, negotiating, reviewing, and redlining commercial agreements, including Master Services Agreements (MSAs), Non-Disclosure Agreements (NDAs), and Data Processing Agreements (DPAs).
• Excellent written and verbal communication skills with exceptional attention to detail.
• Strong analytical and problem-solving abilities with the capability to translate legal expertise into structured, actionable feedback.
• Demonstrated interest in legal innovation and emerging technologies.
• Experience collaborating with cross-functional teams in fast-paced environments.

Preferred Qualifications

• Previous experience working with AI, legal technology platforms, or AI training and evaluation projects.
• Background in a corporate law firm with experience in Mergers & Acquisitions (M&A) or private equity fund formation.
• Familiarity with legal operations, contract lifecycle management (CLM) platforms, or enterprise contract management solutions.

Benefits

• $90 - $130/hour pay
• Remote work opportunity