Senior Counsel, Labor and Employment
Quick Summary
1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people.
1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.
But we're going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. 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 L&E matters, including hiring practices, performance management, separations, leaves and accommodations, investigations, wage and hour compliance, and other key areas
- Build L&E 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 L&E 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 L&E 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.
What We Offer
~2 min readListing Details
- Posted
- March 23, 2026
- First seen
- March 25, 2026
- Last seen
- April 22, 2026
Posting Health
- Days active
- 28
- Repost count
- 0
- Trust Level
- 51%
- Scored at
- April 22, 2026
Signal breakdown

We're building a new mental healthcare system. Tens of millions of Americans seek mental health care every day, but the vast majority never get the care they need. Headway is solving this, and we’re doing it all through software.
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