Senior Counsel, Corporate & Risk

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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, Spark Capital, 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 Counsel, Corporate & Risk, you will be a key strategic partner to Headway’s Procurement, Finance, Customer Experience, and Communications teams during a pivotal growth phase for the company. In this role, you will gain broad in-house exposure across Headway’s third-party contracting, disputes and escalated requests, corporate insurance, and other corporate and risk matters (reporting to the Associate General Counsel, Commercial and Corporate). This is a unique opportunity to join a mission-driven healthcare technology company; work alongside world-class colleagues; and in an environment where Legal is viewed as a true strategic partner — and where our investment in AI will drive your growth in operating at ‘top-of-license.’

You will own

• Third-party and vendor contracting — building out and leading our agentic first-pass contract review, while serving as DRI on escalations and exceptions that reflect our goals and priorities.

• A key subset of disputes and escalated requests — e.g., patient cost disputes, escalated provider matters, administrative/regulatory inquiries, and escalated document and records requests — partnering closely with Customer Experience and Communications to resolve effectively.

• Headway’s annual corporate insurance cycle and ongoing insurance administration.

• Other corporate and risk matters that arise within a fast-growing start-up environment.

You’d be a great fit if you have

• 5+ years of legal experience, including at least 2 years in-house

• Experience in a fast-paced, high-growth start-up environment (healthcare preferred)

• Hands-on ownership of complex processes like commercial contracting at scale, and the judgment to balance risk and trade-offs with the right mix of fidelity and velocity.

• Strong emotional intelligence — you will be the face of Legal to cross-functional partners on matters that may be escalated, time-sensitive, or both. You are able to build relationships and consensus with colleagues amid competing views and priorities

• Genuine interest in working with AI tooling, and in improving or reinventing the systems you work in (versus simply operating within them)

• Ability to translate complex topics into clear and actionable advice for non-legal stakeholders

• J.D. from an accredited law school and active bar membership in good standing (ability to register as NY in-house counsel required)

COMPREHENSIVE BENEFITS

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com http://findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.