Recommendations to others considering WeTransfer:
There absolutely is no harm in trying it out. It is a free program and doesn't even require an account to send files. Naturally signing up for an account offers some additional features (seeing who has downloaded your file, a central place to find any incoming transfers, etc.), but it is not necessary at all. Similarly, the paid account offers increased transfer sizes (up to 20 GB!) as well as storage, password protection, and other SaaS memberships for Paste and Collect.
If you're annoyed by having to constantly change sharing and sending permissions in SharePoint or OneDrive, can't keep track of all your DropBox accounts, or tired of having your emails bounced due to filetypes or sizes, give WeTransfer a try and see if you prefer the stripped-down, easy-to-use program better. Review collected by and hosted on G2.com.
What problems is WeTransfer solving and how is that benefiting you?
Right now, there's a myriad of ways to send files; email, messaging, Dropbox, Pastebin, Slack, Adobe, Cloud folders, etc. Because so many people use so many different systems, I've found that it's easier to just use WeTransfer to the file into peoples' hands as quickly and as painfully as possible. There's no need for the receiver to create an account, or be granted access, or upgrade permissions, or change your sharing rules or any other of the annoyances that make file transfers a pain. WeTransfer makes it easy for the recipient to download the file quickly and easily.
Also, WeTransfer doesn't really care what you upload to it; documents, pictures, (short) videos, entire folders of mixed documents, etc. I haven't tried sending programs through the service, but I've been able to send clients and contractors everything from event flyers and marketing images to entire folders filled with video clips, photos, Word documents, and PDFs. Review collected by and hosted on G2.com.