Pros
The people are the best people you will ever work with. The teams are fun, engaging, intelligent, and just get it. It's unlimited PTO and they mean it, you can take a week off per month as long as you're hitting quota. They have great benefits, fun culture workshops every month, and their internal tools are amazing and make your work super efficient. Some of my favorite mentors came from Heap. The onboarding, enablement, and continuous development is unmatched. They really teach you how to be the best you can be. They don't micromanage. The leadership is motivating and inspiring, but will also call you on your sh!t. You can tell they really care about you as a person.
The former CEO, Ken Fine, is the kindest, most intelligent, happiest person I've ever met. I want to work wherever he goes next.
Cons
Honestly, the only con was the fact that they got acquired by Contentsquare. I miss Heap and my team everyday I'm not there. We all had high hopes in the beginning, but then they laid off some of our best leaders to keep some of their worst. It was like seeing this beautiful ship you've built with all your best friends and mentors get slowly set afire and torn to pieces by the cannons of disorganization launched by CS. It's not any one person's fault that this happened. I think the biggest disappointment was CS's lack of enablement, professional development, cross-team collaboration, and occasional poor quality of hires.
I wanted a lifelong career at Heap. I had plans to work there for years, maybe even decades if I could. But that all went down the drain when they got acquired. Everything changed, promotions got put on hold, morale was lost, processes were delayed, teams were reshuffled, and the best employees were let go. I eventually had to take a role somewhere else because I wanted more career development that Heap promised, but CS did not.