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: First off, I'm kind of surprised by the low ratings here. I realize I say "genuinely" a lot, but I'm not sure how to stress how much I feel what I'm saying. It's a pretty in-depth review, but I want to give prospective people insight into the company. From day one, it's been one of my favorite places to work, and it's shocking that the overall rating is about the same as my previous companies. Anyways, the pros are in order for me: - Everyone I talked to during the interview process was refreshingly great people, and all seven-plus of them said the people were their favorite thing about the company. After being here for over a year, I completely agree. Everyone (genuinely everyone) that I work with is empathetic, genuine, mission-oriented, competent, friendly, and low-ego. People who do not fit that archetype are managed out pretty quickly—much quicker than at other companies I've been at. - This take depends on where you've worked before. I come from big tech, and it's one of the chillest places I've worked. It's expected that you have strong ownership and are productive during the workday, but management and cross-functional partners are understanding when things come up and timelines need to change. - My managers—I've had multiple here—and those of my friends' are fantastic. They're kind, low-ego people who genuinely care about your career goals, even if it's to maintain your level and meet expectations. Leadership is also quite good, but not as uniformly great. I feel that leadership does try to do right by everyone; sometimes the execution is bad, but the intention is grounded in a good place. I think a small but vocal group of engineers hold leadership to the bar that children hold their parents to—that they should have the right answer for everything on the first go, but we're all humans trying to find our way on this spinning rock. This isn't unique to Headway, but it is unique to engineering at every company I've been at. For the prospective engineers, our Blind is a ghost town—that in of itself is a signal. - It's a delicate time for engineers as companies are trying to figure out how to leverage AI. Some companies are concerned about cost and limit how many tokens an employee can use; some are betting their future on it and have laid off huge percentages of their staff—but none have figured it out. Leadership here has taken a pretty balanced take in that there is no limit or focus on token productivity, allows engineers to expense personal AI plans, and has not done any layoffs. There was a very-controversial-to-engineers-but-nobody-else token minimum for a month (it's no longer tracked) with a two-month lead up to it, but I understand the desire to push the entire company to adopt AI in their daily workflows. - Pretty strong in-office culture even though it's completely remote. It's fun to go to the office, vibe with and meet people, and eat free lunch. I have never heard anything even be uttered about a push to come to the office, but people, especially fellow engineers, love to speculate. Depending on the role, they've always or have recently started hiring in-office hubs. - I'm kind of whatever on the mission, but it is a very mission-oriented company and people here very much align with it. Like it's a great mission and all—I'm just not a mission-motivated person.

Cons: Compared to the cons at other companies, these feel pretty tame. They're also in order of how I care about them: - The business is doing well, but it feels like there are pretty significant headwinds and business gaps between where we are and IPO. I've only worked at public companies, so maybe this is normal for pre-IPO companies. One of my previous companies almost could not raise money during one late-stage round, but now it's public, profitable, and worth many, many billions. So it could just be par for the course? - It's a very collaborative and "make space for everyone" culture, but that leads to death by committee and deliberation. Everyone is pretty smart, so all the ideas are pretty good, but they just go in conflicting directions. Leadership also often does not align internally ahead of time, so teams will get thrashed via the telephone game. My hot take is that most people have an irrelevant, even if good, opinion in most discussions. - It's pretty chaotic. We have not figured out how to plan work at a multi-team level. Concrete roadmaps are nonexistent, and the ones that try to get made are irrelevant in a month. I think this is par for the stage of the company, but it's genuinely pretty jarring. It is improving though, and managers try to insulate teams from it as best as they can. - It's a very regulated space, and the company goes to great lengths for legal and clinical compliance. Unfortunately, these areas are pretty understaffed, so the amount of critical work that is blocked by their approval can be unreal at times. - I think the CEO would benefit from executive coaching. It's clear that he wants to be a down-to-earth and relatable person, but the company is at a size where being candid creates more thrash than necessary. To be clear, I feel every CEO of a successful company has to bite this bullet at some point, and it's hard to let go of the startup family vibes for a corporate vibe.