Headway

6 open remote positions

Headway is building a new mental healthcare system that makes therapy affordable by automating insurance admin work. They are a Series D company with over 75,000 providers and 1 million patients served, backed by top investors, and focused on high-impact culture.

Salary Distribution 6 of 6 jobs

PTO Distribution 4 of 6 jobs

Unlimited PTO 4 jobs (67%)

Parental Leave Distribution

Maternity Leave 4 jobs

16w
16w
16w

Paternity Leave 4 jobs

16w
16w
16w

Benefits Overview 4 of 6 jobs

Dental (4) Equity (4) Medical (4) Parental Leave (4) Vision (4) EAP (3) Therapy Reimbursement (3) Training (3) 401(k) (2) 401K (2) Fertility (2) Flexible PTO (2) HSA/FSA (2) WFH Stipend (2) FSA (1) Fertility Benefit (1) HSA (1) Holidays (1) PTO (1) Paid Holidays (1)

Open Positions

Director of Customer Experience (CX) Operations

$160,000–$250,000/yr
US Unlimited PTO 16w maternity 16w paternity

  • Lead the entire CX operation across Agent Success, Customer Care, Programs, and Systems, with over 100 employees and 800 partner agents.
  • Own the customer experience end-to-end, setting standards and scorecards, and bringing AI into operations for better support.
  • Manage capacity, cost, and the support engine including training, QA, and technology, while being the customer's voice in R&D.

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Senior Associate, Payer Strategy & Ops

$90,440–$133,000/yr
US Unlimited PTO 16w maternity 16w paternity

  • You will own the production of commercial KPIs and competitive intelligence resources for the payer commercial team.
  • You will drive coordination of commercial reporting cycles and enablement infrastructure for the payer partnerships org.
  • You will work on critical strategic workstreams that power the commercial operating system, using AI tools to enhance outputs.

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Staff Software Engineer - Insurance

$224,000–$336,000/yr
US Unlimited PTO 16w maternity 16w paternity

  • Lead design and implementation of systems powering Headway's insurance operations, including patient identification, pricing estimates, provider matching, and claims.
  • Build data-intensive, ML-powered platforms that serve patients and providers and learn from every visit.
  • Mentor engineers and write high-impact code at the intersection of healthcare data and payer operations.

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Contract Technical Recruiter

$80–$100/hr
US

  • Support full-cycle searches across the engineering org, spanning aggressive sourcing and strategic close motions.
  • Partner closely with Senior Recruiters, coordinators, interviewers, and hiring managers to drive predictable hiring outcomes.
  • Deliver an exceptional candidate experience through every step of the process, ensuring consistency and raising the hiring bar.

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