Full-Time

Customer Care Associate

Posted on 9/27/2025

Headway

Headway

1,001-5,000 employees

Connects patients with in-network therapists

Compensation Overview

$29.64 - $32.93/hr

Remote in USA

Remote

Remote across the US; option to work from offices in New York City, San Francisco, and Seattle.

Category
Operations & Logistics (3)
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Requirements
  • Strong verbal and written communication skills with ability to explain complex concepts clearly
  • Empathy and problem-solving skills to assist providers and patients
  • Ability to handle high-pressure client-facing situations and de-escalate
  • Good judgment and discretion, integrity in decision making
  • Ability to meet and exceed tactical goals while maintaining quality
  • Interest or prior experience in healthcare technology or healthcare industry
Responsibilities
  • Deliver on the Headway promise by helping providers and patients through issues encountered along their Headway user journey
  • Resolve inquiries for providers and patients via email, live chat and phone daily, Mon-Fri 9 AM - 6 PM across US time zones, consulting available resources and team
  • Continuously learn and upskill by staying up-to-speed on Headway’s evolving product and service and insurance practices
  • Advocate for providers and patients by surfacing frictions in customer experience and proposing process and product iterations to improve Headway’s mission
Desired Qualifications
  • Experience in customer support or care roles in healthcare or tech-enabled services
  • Experience with insurance practices or healthcare billing
  • Experience with headway products or similar platforms
  • Ability to manage multiple conversations and priorities simultaneously

Headway builds a platform that makes mental healthcare easier to access and afford. For individuals, it helps users find therapists and psychiatrists who accept their insurance, letting them filter by preferences and compare thousands of providers so out-of-pocket costs are lower. For providers, it reduces administrative work related to insurance, enabling in-network care without the bureaucratic hassle. The product connects patients and providers through insurance-enabled matching and handles the related paperwork and billing so care can be more affordable and straightforward. Unlike networks that only list providers, Headway actively streamlines both sides of the process by coordinating with health plans and practices to maximize in-network care. The goal is to create a system where finding, paying for, and receiving therapy is simple, affordable, and accessible for more people.

Company Size

1,001-5,000

Company Stage

Late Stage VC

Total Funding

$327M

Headquarters

New York City, New York

Founded

2019

Simplify Jobs

Simplify's Take

What believers are saying

  • Headway raised $100M Series D at $2.3B valuation from Spark Capital.
  • Headway partners with Cigna and Blues to cover all 50 states.
  • Headway acquires Tezi team to advance human-centered AI in care.

What critics are saying

  • Grow Therapy undercuts Headway by accepting Medicaid and Medicare.
  • Lyra Health's denser psychiatrist network causes Headway patient abandonment.
  • Spring Health dominates employer plans with integrated Medicaid support.

What makes Headway unique

  • Headway connects patients to 34,000 insurance-accepting providers nationwide.
  • Headway handles insurance paperwork, freeing providers for patient care.
  • Headway integrates AI-assisted notes and telehealth in expanded EHR.

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Benefits

Equity Compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave for eligible employees

Carrot Fertility annual reimbursement and membership

13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st

Flexible Paid Time Off

Employee Assistance Program (EAP)

Training and professional development

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

1%
PR Newswire
Mar 31st, 2026
Headway Acquires Team Behind Tezi to Advance Human-Centered AI in Mental Health Care

/PRNewswire/ -- Headway, the company building a new mental healthcare system that everyone can access, today announced the acquisition of the team behind Tezi,...

GIANT Health
Sep 9th, 2025
Headway expands EHR with AI-assisted notes, embedded telehealth

Headway, a platform connecting patients with mental health providers covered by insurance, announced expanded EHR features for providers.

FxDailyInfo
May 25th, 2025
Headway Recognized as The Best Global Forex Broker 2025

May 25, 2025 - ForexDailyInfo.com, a leading authority in the forex industry, is proud to announce that Headway has been officially awarded the prestigious title of "The Best Global Forex Broker 2025".

Headway
Apr 4th, 2025
New Award: Headway Recognized for the Best Partners Program 2025

Last month, Headway received a brand-new award - "Best Partners Program 2025."

Nava Benefits
Mar 6th, 2025
Nava + Headway: redefining access to mental healthcare

That's why navabenefits.com is thrilled to announce its partnership with Headway, a company redefining how mental healthcare is delivered.

INACTIVE