Pros
Remote work. Amazing, helpful and incredibly talented colleagues.
Cons
It’s hard to pinpoint what went so wrong. 2-3yrs ago, coaches felt heard and respected. Even with layoffs happening, it seemed like we were still passionate about the mission while pushing the company forward. Slowly but surely, benefits started being taken away. $300+/month for wellness down to $50, comprehensive medical coverage turned into services that were barely covered, loss of 401k matching, Unlimited time off to what felt like The Hunger Games of getting a proper vacation. From $2k yearly raises to nothing. No promotions, no incentives. But volume? That grew. Coaches expected to deliver live mental health sessions simultaneously with 4, 5 and 6+ people. The past year barreled into what became one of the worst places I’ve worked. Coaches had a culture that allowed for mutual support, mentorship and friendship. Endless steps of clocking in and out, limited breaks, systems that break down constantly, no support, lots of apologies but no improvements in sight. For the coaches that were left with 5 hours, the new workflow now includes 13 (YES THIRTEEN) status changes on 2 different systems which can easily double since it is also expected that each status change is posted on slack. What in the digital sweatshop?! The most recent slap in the face was in June 2025, when 25%-30% of the coaching team received an email where they were informed their full time positions were now being changed to part time starting with 5 hours a week. FIVE HOURS A WEEK. Not enough to pay for groceries but enough to avoid reporting yet another layoff. As expected, many of those coaches voluntarily quit and others who weren’t affected were so impacted by this callousness that they voluntarily left. The glitches, low tech platform, poor leadership, constant experiments and throwing of the noodle to see what sticks continues. Endless spreadsheets, so many spreadsheets. And on top of it we have to hear from one manager that she loves us after every announcement. It has been months since coaches have heard from their managers, or had processing group meetings. It’s just announcements with changes all the time but a complete disconnect. It’s hard to even guess where Headspace is going but what I do know is that after 2 decades in mental health, I can confidently say they have made sure that I never want to work in this field again.