Pros
When Sears was "Sears" it was a great place to work because of the leadership and the name behind the company. Sears is not a bad place to start a career for a college graduate but don't expect to become successful and place Sears on your resume and receive good feedback.
Cons
Once Sears merged with Kmart, everything changed. There is constant bickering amidst whether or not you are a "Sears" person or a "Kmart" person. Although they list hundreds of jobs on their career site, Sears is tremendously bad at promoting people from within and recognizing or taking care of associates who have been dedicated and true to the organization. The management style is "manage by intimidation" and they leave very little room for personal growth. They are extrememly behind technologically and unfortunately fail to retain top talent because of their lack of opportunities. Management does not trust the work force and they treat the majority of associates like they were rebellious teenagers who need constant micro managing.