Legal Operations Lead

🕒 August 7

🗽 New York – Remote

🗽 New York – Remote

💵 $95.2k - $140k / year

⏰ Full Time

🟠 Senior

⚙️ Operations

👻 Ghost score 0%

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• 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