Headway

What is Headway?

Headway is building a new mental healthcare system that makes it easy for therapists to accept insurance and grow their practices, while connecting patients with affordable, in-network mental health providers. Founded in 2019 and headquartered in New York, Headway has rapidly scaled to serve patients across all 50 US states, addressing the critical shortage of accessible mental health care.

The platform handles the complex administrative burden of insurance credentialing, billing, and scheduling so that therapists can focus on what they do best — helping people. Headway has raised $327 million in funding and is valued at $2.3 billion, making it one of the most important companies in the mental health space.

Where will I work?

Headway is a remote-first company with employees distributed across the United States. Optional offices are available in New York City, San Francisco, and Seattle for those who prefer in-person collaboration, but there is no requirement to work from an office. The company embraces flexible, remote work as a core part of its culture.

What is the Headway team like?

With approximately 3,900 employees, Headway has grown rapidly while maintaining a mission-driven culture focused on fixing mental healthcare in America. The team spans engineering, product, operations, clinical partnerships, and customer support. Employees are united by the belief that everyone deserves access to quality mental health care regardless of their insurance or financial situation.

Work-Life Balance

Headway offers unlimited PTO, empowering employees to take time off whenever they need it. All full-time employees also receive 56 hours (7 days) of dedicated sick time at the start of each calendar year. The remote-first setup and flexible scheduling give employees significant autonomy over their work-life balance.

Perks and Benefits

• Unlimited PTO plus 7 days dedicated sick time
• 4 Cigna medical plans (employer covers majority of premiums)
• 3 Cigna dental plans
• HRA reimbursing up to $2,100/year for mental health copays and therapy
• Employer-paid life insurance (100% of salary up to $500K)
• Disability insurance (short-term and long-term)
• 401(k) and Roth retirement plans
• Equity compensation
• Up to 16 weeks fully paid parental leave for primary caregivers
• Annual work-from-home stipend
• Monthly telecommunications stipend
• $500 annual professional development stipend