Pros
The CEO, Ben Congleton, is a huge fan of the Zappos-style Delivering Happiness movement. I've never met someone so personally dedicated to the concept of keeping employees happy to make happy customers. One thing that has really stood out is how much autonomy we all have. Olark really lets you push forward your own ideas because everyone trusts each other to have the company's best interests at heart, which has never failed to be true. And you can rely on your coworkers to have your back when you're taking a risk. The team is great. Olark manages to attract talented people who are a lot of fun to work with. I never felt as cared for by my coworkers as I have at Olark. A big advantage for me is that Olark is a virtual company, that is you can work from anywhere, and you get to choose your own hours. That flexibility has let me manage my own life like no other company has. A lot of coworkers really take advantage by travelling and working wherever they want. The CEO himself always seems to be somewhere different visiting family or friends. I mean, talk about work/life balance. If I could rate the company 10 stars I would. You'd think with so much flexibility nothing would get done, but the company is doubling every year on revenue. Olark really does know what it is doing. I think because we aren't wasting time and energy figuring out what's worth doing, we have the luxury of not killing ourselves working. How many tech companies can you say are like that? tl;r We are crushing it so hard that we are living our lives awesomely.
Cons
I guess if I had to say a con, working virtually can be difficult if you're not ready for it. Olark lets you fly to hang out with coworkers when you want to or need to, and we have a great Skype and HipChat culture, but the rest is up to you.