Pros: - A bright engineering team. - An empathetic culture and good compensation and 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, and this is no exception. We struggle with planning and prioritization, and the communications from leadership aren't perfect, but overall, the people and the work make up for the pitfalls.

Pros: I’ve been with Headway since December 2020, and it is undoubtedly the best company I have ever worked for. Over the years, I’ve had the opportunity to work on deeply fulfilling projects while watching the organization expand significantly. The most rewarding aspect is knowing our work directly helps millions of people. Internally, the company treats its team exceptionally well. I have consistently felt that my work is respected and, more importantly, that I am valued as an individual rather than just a metric of output.

Cons: Because we are scaling so quickly, company priorities can shift rapidly. This means project roadmaps occasionally change abruptly, which can be frustrating when it leads to sudden pivots or having to walk away from work you've heavily invested in.

Pros: Headway is a genuinely fun place to work, and a lot of that comes from the people. Engineers are heavily invested in building a good product and are quick to help. The company has a strong mission, which makes work feel meaningful.

Cons: There are still some startup growing pains. Priorities can shift suddenly, which sometimes means changing direction mid-project. Depending on how you like to work, that's either exciting or frustrating. It keeps things moving, but it can be hard to plan around.