Pros
Superior product and service to the competition. Some more complex solution sales are possible for sometimes a lot more money (not so much for geographic reps, though, more for Major Account Reps). Depending on your manager, you may have a lot of flexibility in how you run your day or week. A good place to start a sales career, but most will move on to something better within three years (although the company has recently changed their hiring to focus on experienced solution sales reps).
Cons
The biggest challenge is that 80% of your business comes from lease renewals of postage meters, and so you depend on what your manager gives you as a territory. If you happen to not have many leases coming due in your territory, then you can kick ass with new applications, competitive conversions, and new meter placements, but you can still end the year nowhere close to making quota. Nobody on my team is making quota year-to-date. There are no consistent performers among the geographic reps in the district (Major Account Reps are insulated from some of the challenges of the geographic reps). Less than 9% of geographic reps made quota in 2009, and then they raised quota by 9% in 2010. The company is also pushing us to sell services that don't count towards quota--while you get paid on it, it doesn't help the very important quota-portion of your comp plan. The mailing industry is shrinking--the USPS projects a 30% decline in First Class Mail over the next ten years, which directly impacts our sales of postage meters, which is 80%+ of our sales. Many of the small- to mid-sized businesses are downsizing their meters, going back to stamps, or outsourcing the processing of their mail. Pitney Bowes makes everything much more complicated than needed, which sucks away your time from selling. Finally, my laptop is 8 years old and feels on the brink of dying.