Pros
The people at Outreach are fun, genuine, and smart. There are a lot of complex engineering problems to tackle as the business scales.
Cons
Filter Glassdoor reviews by Engineering or Product; how many reviews do you see? Probably not a lot. There is no clear long term strategy articulated by leadership. Quarterly priorities from the bottom don't map to top-down goals from leadership in any noticeable way. Engineers and Product Managers are spread thin and overworked. Morale has been worsening due to shifting priorities, lack of processes, and the constant barrage of incidents (look at status dot outreach dot io to see what I mean). You will more likely than naught deal with tech debt or untangling the decisions made by folks years ago than working on bleeding-edge features. A lot of hiring recently has been from big companies like Microsoft, and Amazon, so the culture has morphed and is becoming less collaborative and more political/adversarial.