Headway
Headway
501 – 1,000 Employees
HealthcareMarketplaceSaaS
Headway is a healthcare technology company operating an insurance-native marketplace for mental health care. Its platform connects people with licensed therapists and psychiatrists for in-person and online appointments, helping users find providers by specialty, location, and insurance coverage. Headway also manages insurance verification and billing, while giving providers tools such as a provider portal and insurance-native electronic health records system to reduce administrative work. The company partners with more than 100 insurance plans, supports care in multiple languages, and focuses on making in-network mental health services more accessible and affordable. Headway’s team works across healthcare, marketplace, and SaaS products, with hiring opportunities centered on technology and services that improve access to behavioral health care.

Senior Corporate and Risk Counsel at Headway (Remote, United States)

Lead corporate and risk legal work for Headway’s mental healthcare technology platform, including vendor contracts, disputes, and insurance. Advise cross-functional teams as the company scales.

Description

  • Partner strategically with Procurement, Finance, Customer Experience, and Communications.
  • Lead third-party and vendor contracting.
  • Develop and manage agentic first-pass contract review.
  • Own contract escalations and exceptions as the directly responsible individual.
  • Manage selected disputes and escalated requests, including patient cost disputes, provider matters, administrative and regulatory inquiries, and document and records requests.
  • Work with Customer Experience and Communications to resolve escalated issues.
  • Manage Headway’s annual corporate insurance cycle and ongoing insurance administration.
  • Address additional corporate and risk matters in a fast-growing startup environment.
  • Report to the Associate General Counsel, Commercial and Corporate.

Requirements

  • At least five years of legal experience, including two or more years in-house.
  • Experience in a fast-paced, high-growth startup; healthcare experience is preferred.
  • Demonstrated ownership of complex processes, including commercial contracting at scale.
  • Sound judgment when balancing risk, trade-offs, accuracy, and speed.
  • Strong emotional intelligence with the ability to build relationships and reach consensus among competing priorities.
  • Genuine interest in using AI tools and improving or reinventing systems.
  • Ability to turn complex legal topics into clear, actionable guidance for non-legal stakeholders.
  • J.D. from an accredited law school.
  • Active bar membership in good standing.
  • Eligibility to register as New York in-house counsel is required.
  • Authorization to work in the United States for any employer.
  • No current or future need for visa sponsorship.

Benefits

  • Comprehensive health and wellness benefits.
  • Retirement savings program.
  • Equity opportunities that provide meaningful ownership.
  • Reasonable accommodations for people with disabilities.