Headway

4 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 4 of 4 jobs

PTO Distribution 3 of 4 jobs

Unlimited PTO 3 jobs (75%)

Parental Leave Distribution

Maternity Leave 3 jobs

16w
16w
16w

Paternity Leave 3 jobs

16w
16w
16w

Benefits Overview 3 of 4 jobs

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