FORTUNE – What do you do with a nine-year-old file-sharing service that trails behind startups like Dropbox and Box? If you're Palo Alto-based YouSendIt CEO Brad Garlinghouse, you change the name, experience, and pricing. With "Hightail," Garlinghouse hopes to attract new users but also have a name hip enough to turn into a user catchphrase.
"We wanted to choose a name that was different and captured this larger vision of where the world was going," Garlinghouse tells Fortune and says it signifies the beginning of a new chapter for the company. The new Hightail desktop, mobile, and web experience will roll out to the company's 43 million-plus users in the coming weeks. A "Lite" option gives users 2 gigabytes (GB) of free storage to house files 50MB or smaller. For $9.99 a month, "Pro" users can store up to 5 GB of files 2GB or smaller. And, in an attempt to trump the competition, a new Pro Plus plan offers unlimited storage of 2GB files for $15.99 per month.
Although formal discussions about making over YouSendIt didn't start until last fall, Garlinghouse already knew a major change was needed when he arrived at the company in May 2012. To the former Yahoo (YHOO) and AOL (AOL) executive, YouSendIt remained a widely used service with more growth potential hampered by a dated user experience and name. So he 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.)
The question now for Garlinghouse is whether the rebranding will be enough. With $49 million in funds raised since it was founded in 2004, YouSendIt is not cash flow positive. And 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. Although, as Garlinghouse quickly notes, YouSendIt has managed to grow its userbase without requiring hundreds of millions of dollars in backing -- a reference to fellow enterprise-focused competitor Box, which raised $150 million during its latest round of funding and is eyeing an IPO by 2014.
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. Indeed, Hightail may not be cash flow positive, but with the rebranding, the company hopes it will have a better shot at competing. Says Garlinghouse simply: "We wanted to be in, be real, and be bold."
To achieve balance he tries to leave work by 2 A.M.
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