Senior Counsel, Corporate & Risk

OpenKrill; United States; Remote; USD 180,000 - 240,000; Full time

Job summary

Headway is seeking a Counsel, Corporate & Risk to serve as a strategic partner across procurement, finance, customer experience, and communications. You will own third-party contracting, manage disputes, oversee insurance cycles, and handle various corporate risk matters in a fast-growing startup environment.

Ideal candidates have 5+ years of legal experience (2+ in-house), a JD from an accredited law school, and the ability to translate complex topics for non-legal stakeholders.

Qualifications

• 5+ years legal experience, including 2+ years in-house.
• Experience in fast-growth startups (healthcare preferred).
• Owns complex contracting at scale; balances risk.
• Strong emotional intelligence; cross-functional partner.
• Interest in AI tooling and system improvement.
• Ability to translate complex topics for non-legal stakeholders.
• JD from an accredited law school; NY in-house counsel status.

Responsibilities

• Oversee third-party and vendor contracting.
• Manage disputes and escalated requests with CX and Communications.
• Lead corporate insurance cycle and administration.
• Handle other corporate and risk matters in a startup.

Skills

Legal experience

In-house experience

Contracting

Regulatory compliance

Cross-functional collaboration

Education

J.D.

Job description

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 85,000 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, 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)

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