Pros
Sears is a great place to move laterally between functions. You could spend an entire career at Sears Holdings, never leaving the Hoffman Estates headquarters, and easily work in 10 different functional roles. It is a highly centralized organization which promotes networking between functional areas around product or format lines. People routinely move from marketing to inventory to merchansiding to HR or any other path they see fit. The benefits are decent, good health and dental plans are available.
Cons
There pay is below industry average in many fields, especially if you are not in merchandising. Annual bonuses are offered but the probability of achieving the corporate payout goals are very slim unless you work for the Lands End or Home Services divisions. Staffing is a nightmare and employees are often asked to do the work of 2-3 employees. Corporate politics are prevelant and often play a role in job promotions or access to resources. If you are good at networking this can be a plus but it is definitly not a meritocracy.