Pros
Outreach as a company has a ton of potential. Good product market fit, experienced leadership, great talents, but overall turns out to be a really tough place to work.
Cons
Leadership, all the way down from the CEO, encourages a culture of arrogance. Outreach's product is better than the competitors but rather than speaking to our products strengths, leadership will make ad hominem attacks on the competitor (as if no one can do anything better than Outreach). Benefits are poor for the industry, and keep getting worse. When I started a 401k match "was being discussed" but it's still not offered. Health coverage continues to get more and more expensive every year, and little more is offered from a benefits package. The Outreach product, while being the market leader, has so many issues making it incredibly hard to work with customers and keep them happy. This fails to be recognized or fixed. Rapid growth led to rapid hiring and filling vacancies with subpar talent. Middle management is not just bad, it's abysmal. Micromanagement is rampant and there is little to no recognition for good work. Finally, the company practices an odd form of idol worship with the CEO despite rarely hearing from him outside of a weekly company wide email with little substance and prerecorded videos of him. It's super strange. There are many other challenges and cultural issues, but these are the most pervasive and off putting.