Arik Hesseldahl

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In New Challenge to Dropbox and Box, YouSendIt Morphs Into Hightail

hightail-formerly-yousenditIt may have been awhile since you’ve thought about YouSendIt, the cloud-based file-sharing service that has been around since the middle of the last decade. For all that time, it has been best known for coming in handy when you had to send someone an email attachment that was too big for the company email server, or even for Gmail.

But time has moved on, and now there are so many file-sharing services in the cloud — Dropbox, Box, Google Drive and the like — that sending large attachments has kind of become beside the point. YouSendIt has been humming along quietly, having carved out an early and loyal niche of business users. A trusted brand name, it has 43 million people — free and paid — using it around the world, in 193 countries. And, of course, in that time, its service has grown far beyond the paradigm of “sending large attachments,” but the name sort of places fences around how you’re inclined to think about it.

“The name constrained our product breadth,” CEO Brad Garlinghouse told me. “It didn’t indicate our current product breadth, let alone where we were headed.”

So a new name was created, with a little help from Siegel+Gale, and is part of a broader shake-up of the company’s business that Garlinghouse has been working on since taking over as CEO last year. He’s a former senior VP at Yahoo, where his portfolio included Yahoo Mail and its other communications products. He was also president of consumer applications at AOL.

Today, YouSendIt is changing its name to Hightail, and is rebranding itself as more of a broad-based file-sharing and collaboration service. It’s also throwing down the gauntlet to other services in the space: For $15.99 a month, it’s offering unlimited file storage.

“The name gives us a chance to differentiate in the marketplace,” Garlinghouse said. “There are a lot of companies with ‘box’ or ‘sync’ or ‘drive’ in their name. There’s a lot of blue logos and names in this space. It’s starting to get pretty homogenous.” DropBox and Box? He’s looking at you.

The business goes well beyond storage, Garlinghouse said, though the fact is that the others see it in broader terms, as well. Other services he said, charge tiered pricing for more capacity. “Over the long term that’s not a great business,” he said. “Our view is that we should try to be different from the others around the application, around what you can do with your files.” Among the features the company has added over the years are digital signatures, annotation, management, and notification when a recipient has seen a document they’ve been sent.

The relaunch includes a new mobile presence, including apps on Apple’s iPhone and iPad, plus Android phones and tablets and Windows Phone 8. That’s on top of existing desktop apps for Windows and Mac, plus plugins for Microsoft Outlook and Mozilla’s Thunderbird email client.

And there are bigger plans. Earlier this year, YouSendIt acquired Found, a company that makes a desktop application on the Mac that unifies several cloud storage services into a single environment. It supports services like Google’s Gmail, Evernote, Google Drive, Dropbox and Microsoft’s SkyDrive, and makes files stored in them searchable within a single unified interface. “As there are more cloud services, you end up with stuff everywhere, and it’s hard to find,” Garlinghouse said. Expect more developments on that front later this year.

And say what you will about whether this rebranding effort will work — the fact is that the company is restarting itself from a fairly strong position. It raised about $50 million in venture capital funding over five years, but its last round, a Series D, was in early 2010. Garlinghouse said he doesn’t expect to be raising money anytime soon. “We’re not quite cash-flow positive, but we’ve been judicious in our spending,” he said.


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