Compared to WeTransfers free service, DropSend is a very easy-to-use free service that allows you to quickly send large files of up to 4 GB, which is twice the limit on WeTransfer. Though DropSend allows only 5 files per month and uploaded files expire in 7 days, as opposed to WeTransfers unlimited.
Compared to WeTransfers priced plan at $10 per month, which gives you 50 GB cloud storage and unlimited uploads of files up to 10 GB expiring in 30 days, HighTail, for $15.99 a month, gives you unlimited cloud storage and will accept uploads of files up to 25 GB in size. Hightail has a range of security features for sharing files, provides confirmation of document delivery, has simple file-syncing and supports basic collaboration on visual files. Though the functionality is fragmented across multiple apps and doesnt show file sizes when uploading (the recipient must download the files to view them).