Unicorn Startup with a Top Tier Exec Team - Senior Software Engineer Headway (NY) Employee Review

5.0
Jun 23, 2026
Recommend
CEO approval
Business Outlook

Pros

- Bright engineering team - Empathetic culture and good compensation / benefits - First time founder energy surrounded by industry veterans - Varied work surfaces give a ton of different work experiences depending on the team

Cons

No startup is perfect, this is no exception. We struggle with planning and prioritization, the comms from leadership aren't perfect, but overall the people and the work make up for the pitfalls

Explore other reviews about Headway (NY)

5.0
Jul 7, 2026
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

Flexible schedule and high pay

Cons

They do not provide clients

2.0
Jul 16, 2026
Anonymous employee
Recommend
CEO approval
Business Outlook

Pros

- Some really great, genuine people working here that are committed to the mission. - Early on, they recognized and promoted top performers but this has stagnated.

Cons

- Mission is used to take advantage of people and make them feel guilty for setting boundaries. Mental health matters for everyone else. - Overly focused on AI despite glaring issues and serious ethical concerns with AI being even remotely involved in mental healthcare. Forced unreasonably high token usage or else. I remember a strong focus on providing a "human touch" for therapists and clients but that is almost gone entirely, apart from agents offshore who have no understanding of the US healthcare system and it's complexities. - Recent leadership hires are subpar at best. They lack substance and come from companies that no one looks to as examples of good products/services but they try to make Headway just as bad. - High quotas for the sales team to sign new providers without much concern at all for quality, leaving the CX team to clean up the mess while exec blabs on about growth. Headway used to feel different and seemed to want to be different but it's just another cog in the broken US healthcare machine.

2
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