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Mission-driven culture with growth opportunities, but fast pace

Engineering Manager
Current Employee
Has worked at Headway for 2 years
April 16, 2026
New York, NY
5.0
RecommendsPositive OutlookApproves of CEO
Pros
  • Truly a mission-oriented company that does things the right way and wants to help patients and providers.
  • Some of the kindest and most intelligent coworkers you can imagine.
  • Tons of opportunity to grow your career and experience due to rapid scaling creating new opportunities every day.

It's honestly a joy to be an EM here because the team is so strong due to a consistently high talent bar and huge focus during hiring on cultural alignment.

Cons

Aiming to be peers with really prestigious tech companies and AI labs, but the pay is still more B-tier tech (please add a 401(k) match!).

Rapid growth means processes break before they can get fixed or replaced.

The pace can get crazy, and a high-ownership culture can make work-life balance hard as you try to juggle the opportunities made available to you.

Advice to Management

Keep figuring out how to enable a consistent hiring culture to maintain the people that make Headway special as it gets bigger.

Additional Ratings

Work/Life Balance
3.0
Culture and Values
5.0
Diversity, Equity, and Inclusion
5.0
Career Opportunities
5.0
Compensation and Benefits
4.0
Senior Management
4.0

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