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Inspiring team culture with complex healthcare challenges

Engineering Manger
Current Employee
Has worked at Headway for 2 years
May 26, 2026
San Francisco, CA
5.0
RecommendsPositive OutlookApproves of CEO
Pros

The people are easily the best part: talented, low-ego, and genuinely invested in each other's success. We're helping people get access to mental healthcare, and that shows up in the work in a real way that inspires what we do every day. Headway is also fully leaning into leveraging AI in our daily workflow, which makes it an incredibly exciting place to build.

Cons

Healthcare is heavily regulated, so you can't always ship the obvious thing because there are real constraints, and navigation can feel slow if you're coming from a consumer pace.

The user base is also wildly broad, including patients, providers, group practices, payers, and internal ops. That means getting the long tail right is pretty hard, and what works for one segment often misses another.

Additional Ratings

Work/Life Balance
5.0
Culture and Values
5.0
Diversity, Equity, and Inclusion
5.0
Career Opportunities
5.0
Compensation and Benefits
5.0
Senior Management
4.0

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