Pros
This is a great organization for your first or second opportunity out of college. You'll find that OrderAhead provides you with opportunities that you wouldn't necessarily get at a much larger company. If you work hard and commit the time, you'll find yourself able to work further into what you're specifically interested in, and within a (relatively) short amount of time. You are guaranteed an opportunity to work directly with your team manager on a regular basis, which is a very positive aspect of initial work experience.
OrderAhead is a place where you "earn" what you put in. The ups and downs of the company are a fantastic learning experience that will benefit you in your 3rd or 4th career, and that's important to keep that in mind as you build your resume. The best teammates at OrderAhead are those who are able to focus on their own long-term career goals, and not get too absorbed in team movements, adjustments, etc.
Cons
In exchange for the pros, you'll have to accept the longer hours and lower pay relative to larger startups in the area, especially in your first year. Also, smaller companies are by nature often less organized. Expect to work under a fluctuating environment where areas, like team goals/priorities, change on a semi-frequent (quarterly) basis. You'll go through stretches where you won't be particularly enamored by the work you're doing.