A service I’ve used since the mid 00s is YouSendIt, the freemium file-sharing service you use to send large files to people.

It’s been a perfect tool over the years, especially in the days  when ‘large files’ typically meant anything bigger than about two megs that would give corporate email systems indigestion (if the email carrying the attachment ever made it through, that is).

Today, though, you may think a service like this a bit anachronistic when we have near-ubiquitous cloud storage, 100-meg or faster broadband internet, collaborative working online, etc. Files you want to share with others are often and routinely 20 megs or more  – that’s just a document or a deck – and wait until you get into audio or video files in the hundreds of megs.

The size of a file isn’t a critical thing any more for many people when you simply create, save, and share via the cloud by synchronizing your content through your always-on net connection. You enable others to access that content in the cloud, often in the background or automatically, behaving like a drive on your own computer (think of popular tools like Dropbox or Google Drive that do precisely that).

Yet I have a fondness for YouSendIt.

I still use YouSendIt’s free software for Windows to send files to people when YouSendIt is the most effective way of getting files to them. It’s reliable and efficient. It works well in cases where your recipient can’t access Dropbox or other cloud storage system, typically due to IT-imposed restrictions on their corporate network. With YouSendIt, the service emails your recipient a link to the file awaiting them that they then retrieve.

It’s not always successful – some companies even prevent that behaviour – but for most people, in my experience, it works fine.

Time are rapidly changing, though, with a marketplace that’s exploded into far more than simply sending files to people, clearly the primary reason behind YouSendIt’s re-positioning of its business to challenge the likes of Dropbox in particular, and change of name to Hightail. As Fortune magazine reports:

[…] YouSendIt remained a widely used service with more growth potential hampered by a dated user experience and name. So [CEO Brad Garlinghouse] assigned a 10-person design team to create an all-new user interface and brought in an outside branding firm to help come up with a new name. (Of the four the company tested with customers, “Hightail” earned the highest marks.)

[…] While Hightail’s 43 million-strong userbase isn’t small, it’s a far cry from the 175 million that rapidly growing startup Dropbox trumpeted earlier this week. […] There’s also the issue of whether Hightail will alienate some long-time users who have long since grown comfortable with the old YouSendIt. Garlinghouse admits that may happen with a very small minority but says the new service’s ease of use will earn even more customers.

I’ve been a Dropbox user since it was in beta, and use the depth and breath of its services for my own use and in collaborative sharing with clients and others. In  my experience, it’s the best service of its type.

Earlier this week, Dropbox moved its needle significantly with its announcement of the Dropbox Platform at its first developer conference “to connect the world’s apps, devices, and services.”

Hightail has a tall order to fill. But, this is a rapidly-evolving marketplace; if they build a better mousetrap – which really means, if they offer a more rewarding user experience – they may well attract those more customers CEO Brad Garlinghouse talks about.

As for the new name, my first thought was the phrase “hightail it,” as in “get out of here!” or “move fast.” Maybe that’s exactly what they have in mind: I did like how Google’s ad algorithm presented Hightail as the single ad on the results page when I searched for the definition  of “hightail it.”

(Story prompted by TNW’s report: YouSendIt rebrands as Hightail, looks beyond file sharing to rival collaboration software makers)