Pros
Your experience at Uptake will vary depending on what department you're in. If you're on the business side of things, you will have a much better viewpoint than those in the Engineering realm, which constitutes the majority of the company.
Cons
Uptake sounds like a dream job: casual environment, challenging problems to solve, and cutting edge technologies to work with. But it's really a facade: it's just a place that money has been poured into to hire human capital, jack up the valuation, and then either sell or go public so the investors can cash out. You will find dozens of people who have know idea what their job is or how they integrate into the cohesive whole of the company. At first, I thought I was missing something. But after a year I'm forced to conclude there is no cohesive whole: it is just a scheme. I'm glad I've found other employment before this place changes hands and creates a glut in the supply of software engineers on the market in Chicago. The worst part about it is the cronyism and incompetence that haunts the ranks of middle and upper management. There really are great, talented engineers who work here who have been buried by the rituals of panic-driven development. There is no work-life balance here: you will be expected to perform a high amount of repetitive work to satisfy client SOWs. There is no real vision, just getting by from one SOW to another. They also only have one actual client, which makes them highly dictatorial. In short: there is no real product at Uptake. The product is you. You're hired to increase the valuation so it can be sold at a higher price. And they certainly treat you like a piece of flesh.