Pros
Help Scout made me better, period. I was pushed in my craft, pushed in how I communicate and collaborate with a remote team, and encouraged to learn about what it really means to be customer-centric. I always appreciated the candor of leadership in leaning into vulnerability — as a relatively small team in a scale-up, the founders made quick decisions but were always transparent and honest in their approach. It's no secret that craft excellence is revered, and while that can sometimes create the illusion of an impossible bar, it also means that you're surrounded by people who truly care and are doing their best. Initiative is also encouraged — if you see an area of improvement or there's something you'd like to see prioritized — you'll almost always have the full support of the company to make the change. It means if you want to have an impact, you absolutely can. I also appreciated how the leadership team is aligned on having an opinion — nobody is creating process or structure for the sake of it, but instead everything is done with reason — which means that often the company and product rejects the status-quo. It makes Help Scout a truly unique product and place to work. This is supported by the People Team who do an incredible job to make sure that people feel supported and successful in their role.
Cons
As a small company, things change... priorities, strategy, teams. I went through a couple of re-orgs during my time, which feels like the nature of an organization that understands the need to adapt and change as it grows. But that growing pain is uncomfortable and can slow teams down momentarily. I worked closely with the Founders, which I initially found quite uncomfortable, and at times like I was circumventing due process — but eventually (and with the support of the People Team) found that collaboration to be hugely beneficial and a key contributor to my success. But leaning into that discomfort was certainly not an easy process.
