Pros
Olark is a wonderful company to work for. I feel so lucky to belong to a company that feels like a real team, full of people who are truly psyched to make Olark customers happy and continually strive to improve our service. The founders are actively involved in all facets of the company and no one is 'too little' for regular 1 to 1 meetings with them. Work/life balance is taken very seriously here and you'll never be given any trouble for taking a personal day. We're a distributed team, so there are people working from all over the world along with two offices in San Francisco and Ann Arbor. Weekly team syncs keep us connected and the beginning of every meeting is dedicated to praising teammates for their contributions over the past week. Annual retreats ensure everyone is able to get together in person and have fun as well as collaborate. Every Olarker is involved in customer support regardless of their job title, which keeps the customer and their needs front and center. The whole team is friendly and helpful. I've never felt intimidated about reaching out when necessary, and if I make a mistake I'm encouraged, not reprimanded. Olark is the complete opposite of soulless corporate nightmares I've been a part of in the past.
Cons
Personally I love that there's a ton of freedom at Olark, but I can see how that might be a negative to some. The founders aren't big on hierarchy and it's very rare that you'll have someone telling you exactly what to do and how to do it, so if that's something you need Olark probably isn't right for you. Everyone is trusted to do their job to the best of their ability and ask for help if necessary.