Legal Operations Lead
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Job Description
Legal Operations Lead building AI-enabled workflows and knowledge systems for Headway’s mental healthcare platform. Managing legal operations and cross-functional initiatives during rapid growth.
Responsibilities:
- Design and build AI-assisted legal operations workflows for routing, triage, and answered-question automation outside direct legal advice
- Build an AI-queryable legal knowledge management system producing trustworthy first-draft answers for attorney review and approval
- Project manage the legal component of major company initiatives across Headway
- Oversee daily legal department operations and stakeholder satisfaction
- Identify operational improvements and implement changes using cross-functional stakeholder input
- Own and evolve the legal team’s AI roadmap
- Evaluate, pilot, and implement new legal technology tools
- Maintain a vetted library of prompts, skills, and workflows for recurring legal tasks
- Track department adoption and efficiency gains
Requirements:
- 5+ years of experience in Operations or Project Management within a fast-paced startup environment
- Hands-on experience using AI at work
- Clear understanding of where AI helps and falls short
- Ability to apply AI in Legal and Healthcare contexts is an advantage
- Experience building Operations workflows
- Experience evaluating and implementing AI tooling
- Ability to balance multiple priorities with attention to detail and careful planning
- Ability to execute and build consensus as project manager on major cross-functional initiatives
- Strong communication skills and EQ to navigate competing priorities and build effective partnerships
- Authorization to work in the United States for any employer
- Must disclose whether visa sponsorship is currently or potentially required
Benefits:
- Equity compensation
- Medical, Dental, and Vision coverage
- HSA / FSA
- 401K
- Work-from-Home Stipend
- Therapy Reimbursement
- 16-week parental leave for eligible employees
- Carrot Fertility annual reimbursement and membership
- 13 paid holidays each year
- Holiday Break during the week between December 25th and December 31st
- Flexible PTO
- Employee Assistance Program (EAP)
- Training and professional development
- Robust health and wellness benefits
- Retirement savings
- Meaningful ownership opportunities through equity
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