Senior Counsel, Labor and Employment

Headway
Remote$179k – $280kPosted 24 March 2026

Tech Stack

Job Description

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. As Senior Counsel, Labor Employment, you will be the lead attorney partnering with Headway’s People function to support a rapidly growing and national workforce. You will own day-to-day advice and counsel on employment matters while also working closely with the People team to enhance systems and processes to allow Headway to scale with speed and fidelity. This is a unique opportunity to join a mission-driven healthcare technology company, work alongside passionate and talented colleagues, and grow in an environment where Legal is viewed as a strategic partner. You will: Serve as the primary legal advisor to the People team and business leaders on the full range of LE matters, including hiring practices, performance management, separations, leaves and accommodations, investigations, wage and hour compliance, and other key areas Build LE infrastructure – design and review People-related policies, procedures, and workflows to enhance efficiency and effectiveness Be the in-house subject matter expert, training HRBPs and People managers on LE developments and best-practices Draft, review, and negotiate employment-related agreements and documents Represent the company , including managing outside counsel, in litigation and related disputes You’d be a great fit if: You have 5+ years of post-bar admittance legal experience with a deep understanding of LE matters You have meaningful in-house experience in a fast-paced, high-growth start-up environment You have a deep ability to build relationships and consensus with colleagues amid competing views You have detail-obsession that drives clarity – without missing the forest for the trees You have a J.D. from an accredited law school and active bar membership in good standing (including ability to register as NY in-house counsel) While we prefer candidates based in the New York metro area, we will consider exceptional candidates nationwide. Compensation and Benefits: The expected base pay range for this position is $179,200 - $280,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. Benefits offered include: 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 ... (truncated, view full listing at source)
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