Pros: - Every other Friday off - Unlimited vacation - Decent healthcare - Individuals coworkers are quite nice

Cons: Overall, as a company, Headspace was rather disappointing. While so many of the individuals there are lovely, the company just isn't going in the right direction. The upper-level management either doesn't realize people aren't thrilled or doesn't care. * No interest or effort to retain diversity When I joined, there were 5 female engineers (I'm included in that), at least 3 female managers of engineering teams, a female CEO, and CTO. However, in the merger (more on that below), the board of directors chose to keep the white, male CEO and CTO from the other company instead of keeping either of the female CEO or CTO from Headspace. In my year there, 2 of the female engineers left (plus me), as well as a female engineering manager. There was no effort made to keep any of us. Not long before I left, my team did hire another female, who I lobbied heavily for. If women keep leaving Headspace at this rate, there will be no women to lobby for hiring more. * Poor pay, by industry standards As an L3 (Senior Engineer), I made 160k per year. After a year, when I pointed out that I made 10k+ less than my male counterparts in the same role, I was told there wasn't anything to really be done. * Unclear path for promotions and pay raises In the past year, Headspace has been trying to set up a Total Rewards package, which was supposed to address pay, bonuses, benefits, etc. However, the company hasn't been able to make any concrete progress. Instead of deciding on a useful structure for raises, they just announced a 4% pay raise for 2022. When the CEO was asked about whether that would increase, considering the large inflation rate (6%-7%) in 2021, they said they wouldn't be doing anything different. * Poor project management Last year, the cloud team was tasked with the job of preparing us for a HITRUST audit. For the majority of this project, we had shifting leadership on the team (first no team manager, then a director stepped into a manager position, then promoting a manager internally, then having him leave and having the director manage again, then the manager who just left returning). We also didn't have any team experience on how to do HITRUST. The team worked very, very hard to meet a deadline that was arbitrarily chosen by some level-up upper management. However, even when the team lost two people, the deadline didn't change. Afterwards, when the team had a retro about how we could have improved this project, when our takeaways were presented to upper management, nothing was really done about it. In short, there's really no way for engineers to pass concerns up to management and ever see any change from it. * Mergers and acquisitions are causing chaos In the past 6 months, there have been two mergers, with no real plan to merge the staff, software offerings, operations, etc. * Company mission seems to have pivoted from a "mental health for the world" attitude to "prepare to IPO" For people who joined the company because they were excited about the mission, there is way less reason to stay. Headspace has stopped offering any free meditations, which is a step away from trying to actually improve people's mental health.

Pros: Very mindful approach to work-life balance for engineers that is refreshing. Everyone is very talented and great to work with. Headspace takes a very people-centric focus to employee policies.

Cons: A lot of change and some chaotic project roadmaps. This is mostly due to the merger with Ginger.

Pros: - Very flexible hours. - Lack of vision and leadership makes for easy-to-hit deadlines. - Lots of energizing and fun co-workers. - Incredibly high pay.

Cons: Despite the flexibility and slow-moving nature of the company, this is not a place to grow your career. It's very easy to get stuck here hoping leadership will either be replaced or finally learn how to run a company, as you cheer for the mission. But you realize after a year that you stuck around because of the high salary and vision that will never come to fruition. Leadership is inexperienced and needs to be replaced. No one knows how to run a digital subscription company, and the few external people brought in with this experience always end up leaving within months. The engineering team is a black hole that moves at an inexcusable pace given their size, and nothing major has changed with the product since I joined the team 1.5 years ago. We've tripled in size, but the product has stayed the same. The company is burning cash and not producing subscribers.