Stamps.com is wonderful! It is simply one of the best things out there. Since I've been using it, I have never had to worry about not having a stamp available. Plus, the software reads contacts from Outlook (and has its own internal contact list if you need that) so there isn't a lot of typing. Purchasing new postage is a breeze, and you can view reports of all your printed postage and past purchases.
I've used both... just started using Stamps.com. Can't say enough good things about them! Especially the mail-merge capability for printing labels+postage for newsletters, etc. Saves a world of headaches!
I'll second that! Been using it for 3 months. Saved a lot of money and time compared to Pittney Blows. The updated stamps.com address book can even import from Palm Desktop. Now I have over a 1000 contacts in there with no typing.
Stamps.com has the worst customer service. As long as you don't never need to get them on the phone, good luck. The average wait time is around 30 minutes if you can spare that. They don't offer much of a service in my opinion. They are mostly interested in sucking people in off the internet and forcing them to go beyond their trial period by not answering the phone. By the way the only way to cancel service is by phone. They claim to be an internet company but they don't even have online access to cancel your account. Be careful with this one...
FYI, the results of a little sleuthing on the web.
"How does DYMO Stamps work?
DYMO Stamps software works exclusively with DYMO's top-of-the-line LabelWriter 400 Turbo, Twin Turbo and Duo printers. Through DYMO's postage partner, Endicia, DYMO Stamps users can easily establish a free online account to purchase and print precise amounts of USPS®-approved postage."
The above is off the Dymo site. So effectively, Dymo Stamps is a partnership . So you can either go via Dymo or directly to Endicia. If you select the Dymo route make shore you have the right Dymo printer ... the 300 series does not work with this service. The newer printers start at USD 110 and run out at USD 210 (plus S&T).
If you have the earlier printer, I presume you would have to sign up directly with either Stamps.com or Endicia (i.e. monthly fee plus postage).
As to the original question "Pitney Bowes vs Stamps.com" what is your need today and in the foreseeable future? Piney Bowes invented this market space and has solutions that can grow with the business. The others have only a short history and I question their ability to scale up. Do you home work before you buy!