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Official source last checked September 7, 2026.Remote — United States
Headway
Posted September 7, 2026 · Official source checked September 7, 2026
- Eligible locations
- Not disclosed
- Required time zone
- Not disclosed
- Employment type
- Not disclosed
- Experience
- Not disclosed
- Compensation
- Not disclosed
- Work authorization
- Not disclosed
- Travel
- Not disclosed
- Training
- Not disclosed
- Application
- Company application site
- Listing closes
- October 22, 2026
Headway is hiring a full-time Customer Care Associate to support healthcare providers and patients across the United States. This is a fully remote position open to candidates across all U.S. geographic locations, with optional access to Headway’s New York City and San Francisco offices.
The Customer Care Associate will resolve approximately 40 provider and patient inquiries per day through email, live chat, and phone. Responsibilities include troubleshooting operational and technical issues, helping customers navigate Headway’s platform and insurance-related processes, de-escalating sensitive situations, identifying root causes, and surfacing opportunities to improve the customer experience, internal processes, and product.
Candidates should have excellent written and verbal communication, strong problem-solving skills, sound judgment, empathy, and the ability to perform effectively in a fast-paced healthcare technology environment. Prior healthcare experience or a strong interest in healthcare is valued.
Weekend availability is required. Headway’s support coverage operates Monday–Friday from 9 AM–6 PM ET and Saturday–Sunday from 8 AM–7 PM ET. Occasional weekend and holiday shifts may be required.
Candidates must have a quiet, private workspace with high-speed internet.
This is a full-time remote U.S. opportunity with a base salary range of $54,400–$80,000 USD plus equity. Headway also provides health and wellness benefits and retirement benefits.
Headway
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