Pros
Outbrain is the originator of the "You Might Also Like" widgets that are all over the web today. It is a great company to launch from. You meet lots of advertisers and publishers so there's great opportunities to network while you're at Outbrain. Some of the perks are pretty good: free coffee, free lunch 1 day per week, free snacks (while they last). Most of the people who work at Outbrain are very friendly. There's lots of socializing in the office, including beer cart on Thursdays, when new hires push a beer cart around the office and introduce themselves to the rest of the team.
Cons
For muchof the company's life, they were the only game in town aside from display ads. But now there is major competition in the market, and that is causing some flailing. There is a lot of pressure on sales/accounts to lock in clients, and on product/engineering to copy what competitors do, and on management to ensure constant growth in a very different landscape. As a result, a lot of the original magic has been lost. Outbrain's big claim to a competitive advantage is that they have better quality links than the competition. While that might have been true in the past, Outbrain now shares most of their best advertisers with their competition. So it is kind of moot at this point. The leadership can be arrogant about this. The response seems to be "We invented this space" or "We're the only one with content guidelines." It is not really clear what that means beyond "We have less Cash4Gold links, but they still have plenty of Kim Kardashian and bikini links." But the latter is what seems to offend people most. As a result of the arrogant responses in the face of intense competition, Outbrain is getting out-innovated and losing ground to rivals, including Gravity (owned by AOL) and nRelate (owned by IAC). The biggest threat though, is Taboola, which is actually less than half the size in terms of headcount, but really starting to win the space and seems to be developing better technology.