Almost every single school that does applications online uses the same (horrible) software. And yet for every single school, you must create a new username/password, and fill out the same forms over again, and upload all the same documents.
This is outrageous, not primarily because it's so damned cumbersome, but because there already exists a centralized jobs site: academicjobsonline.org
AcademicJobsOnline is an extension of the centralized service created by the American Mathematical Society, which is open to academics in any field. You upload your documents and personal information once. After that, it takes about 30 seconds to apply to a job. You just check the boxes for the materials you want to include (and have the option of uploading more materials), check the boxes of the letters you want to include, and presto!
Additional benefits to candidates: You can be notified when your letters are uploaded, and it's easy to tailor what you want to send to specific schools (e.g. if you want to send extra teaching letters to certain schools but not to others, all you have to do is check an extra box).
There's also a huge potential benefit to departments: Currently the poor person in charge of sending out letters has to upload letters for (number of applicants) x (number of letter writers per applicant) x (number of schools applied to per applicant). Maybe 2000 letters?? If departments all used this already existing service, this would be cut down to a maximum of (number of applicants) x (number of letter writers per applicant) = maybe 50ish? And I suspect that it could be cut down even further with this service, since it has a box you can check if someone is uploading letters on behalf of the writers, potentially allowing for all the letters to be uploaded in a single bundle.
Seriously, philosophers, the mathematicians already created the service! Let's give [our department administrators] (as well as the applicants) a break!
Having done a quick search of recent JFP listings, let me just say kudos to Duke, Tufts, Yale, Stanford, Tulane, Oregon, and Washington Tacoma, for leading the way. Hopefully next year many more philosophy departments will join them in doing the sensible thing here!