Pros
Working at Outside tends to draw quality contributors, people who like the outdoors and want to build or create something good. Most of the individual contributors across departments are of a high caliber and want to work hard, are friendly, and want to collaborate to create something great. The benefits are really good: unlimited PTO, medical, pro deals, cell phone reimbursement, computer supplied, healthy living reimbursement etc. Being a remote company is a good.
Cons
Leadership in every department is sorely lacking, and the C-suite is lost. The company is run from the top-down, based on the whims of a handful of people, with weak data to back up decisions. The users of their products do not come first. Its clear no one in the C-suite has experience with publishing. (If you want to see both the hollowness of the executives and the insular club in which they reside, look at the fluff PR responses -- signed by all of them? -- they are giving to some of the other glassdoor reviews. It's so fake and should give you insight into their insincerity.) Leadership will often change their mind, requiring teams to rapidly pivot from one project to another. They will give reasons, but they are inconsistent. Everyone working on the project can see the shallowness of the request, reducing faith in leadership. On top of that, everything is urgent and needs to be done immediately, so there is palpable anxiety permeating everyone's mood. The engineering department is a mess. Leadership initiated many changes in vendors, tech, and processes that brought no benefit to the team or product. They implemented an esoteric product philosophy with new jargon that confused or frustrated most of the team. It felt like more time was spent talking about "how to make software" than actually making software. They also pushed "cutting edge" technologies that few understand and have little to no support. They made suggestions not grounded in reality because they are so disconnected from the actual code. Senior engineers and PMs would flag issues to leadership but were swiftly dismissed. Morale is grim, as months and months go by and simple products do not ship. Over-engineering and complexity, complicated processes, and changing requirements disheartened almost everyone. Salaries are all over the map and they will take advantage of you. Once you are hired, do not expect a raise, and if you get one, it probably won't be fair. If you accept a job at Outside, ask for as much as possible out of the gate, as that is your one shot. Depending on your role, it will be hard to move up. Over and over qualified people were not promoted, rather Outside hired people to fill leadership roles. In many areas of the company, it's all CYA, and mentorship is minimal. All in all, I would stay away from this place if you are considering it. Ignore the name and the clout, I guarantee there are much better opportunities.