Start up life is not for everyone, but Headway is pretty solid - Anonymous employee Headway Employee Review

5.0
Apr 27, 2023
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

- The mission is really powerful. I think it attracts very friendly people who respect work life balance more than other tech companies. Everyone seems pretty competent and driven. Overall very positive culture and it seems like everyone is excited to be there. - Lots of opportunities for growth. I've been here a little less than a year and have seen several promotions on my team. There is a clear path for development and my manager spends a lot of time talking to me about my career goals. - Leadership is pretty transparent. They share quite a lot at our weekly All Hands meeting and it makes me feel like I can feel more confident in the company's future. We can ask the executive team anonymous questions.

Cons

- Remote culture can be a bit hit or miss, depending on whether there are other employees in your city. I wish we had a WeWork membership or something to get out of the house more. So many virtual meetings. - It's definitely still a start up and that is not for everyone. It feels like there are frequently new OKRs, leading to big pivots. This is both a pro and a con. I like companies of this size because I can see my impact. If I really wanted stability, I'd go to big tech - but sometimes it can feel a little sudden.

Explore other reviews about Headway

5.0
May 13, 2026
Anonymous employee
Recommend
CEO approval
Business outlook

Pros

I’ve had a genuinely positive experience at Headway. The company is full of smart, kind, mission-oriented people who care deeply about improving access to mental healthcare, and that purpose shows up in the work every day. One of the things I appreciate most is the level of ownership and trust employees are given. If you’re proactive, solutions-oriented, and willing to jump in where needed, there’s a lot of opportunity to make a real impact. Leadership moves quickly, encourages feedback, and is open to evolving processes as the company scales. The culture is collaborative and high-performing without feeling overly corporate. I’ve worked with incredibly thoughtful teammates across departments, and there’s a strong emphasis on continuous improvement, transparency, and building for the long term. Benefits are also genuinely strong and thoughtfully designed, which reflects the company’s investment in employee wellbeing.

Cons

Like any fast-growing company, things can move quickly and priorities can shift. If you thrive in structure and predictability at all times, the pace may feel challenging. But for people who enjoy growth environments and being close to impactful decisions, it’s an exciting place to be.

2.0
Mar 13, 2026
Recommend
CEO approval
Business outlook

Pros

The pay per hour is around $97-137 per hour

Cons

Slow response to resolving issues. Does not send my ANY clients. Getting credentialed for UH has taken well over 6 months. Lost many many clients due to this. I'm still not credentialed with UH

2
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