Pros
Best part of Outreach was leaving. The product is good, but the management is not. Outreach was a hard but satisfying place to work in 2018, but now all the good folks have left or are keeping their heads down trying to ride it out to IPO. There are really hard working good people in the trenches here, propping this place up - like any company, if you're lucky enough to be on a team with a good manager and teammates, it can be alright. Originally this place had A LOT of good people but leadership has driven the vast majority away (so the "former-Outreacher" support groups are pretty good).
Cons
The company runs on burning out its people. People were underwater beforehand and then they laid people off - many of whom had critical tribal knowledge - and expect the rest to pick up the work while also making the working environment worse (RTO, etc). Used at least appear to support modern values like diversity, paternity leave, WFH, equity, but all are on a downward trajectory now. Almost no growth opportunity, and it is systemic, especially in CS: in nearly half a decade at this company, I think I saw maybe 10 out of hundreds of people get promoted to manager, less than 5 people get promoted higher than that. There is absolutely no change accepted from the bottom up - only leadership needs matter, and only as long as the most recent emergency lasts, or who is the loudest bully. Training, enablement, is not provided, it is entirely dependent on the quality of your peers, leaders spend all their time talking with each other in meetings. They had a diversity event for Black History Month where the CEO showed up for 4 minutes to accept credit for promoting diversity, then laid them off the next week. Layoffs were carried out in 10 minute group meetings at 7am. Some people who were not laid off expressed that they wish they had been. Sales, CS, and Ops have awful work-life balance and leaders who are either bullies (Sales) or feckless (CS and Ops). Poor planning (or non-existent planning) leads contributors to work late, work early, and work weekends. Leaders have an idea, want it executed the next week with no project resources, change their mind the next week, and then reverse course again. The office culture in Seattle sucks and just serves the needs of leaders to feel important. Leadership wants the old culture back but doesn't realize it was the people they have driven away that made it what it was. Sr. leadership is extremely insular, cliquey, and doesn't listen to each other or their staff. Silos are MASSIVE. I'll never forget the few attempts at company happy hours (which all were super spreader events) advertised as chances to bond together and then leaders just sat with and talked to each other and their friends.