Why YouSendIt changed its name to “Hightail”

company’s head of marketing explains why the popular file sending service
YouSendIt is changed its name to “Hightail”

YouSendIt has been around
for almost nine years now, which is why changing the name of the company at this stage almost seems crazy. But that’s exactly what the company did two weeks
ago. In a move designed to both advertise its new services as well as take
the competition head on, the company announced that it was changing its name to

It’s the latest in a line
of bold moves ever since CEO Brad Garlinghouse took over. Garlinghouse, is no
stranger to bold moves, back in 2006 when he was a senior vice president at
Yahoo, he penned the infamous Peanut Butter Manifesto about the company
spreading its resources too thin. He also engineered YouSendIt’s acquisition of
the cloud search service, Found.

Mike Trigg,
YouSendIt/Hightail’s chief marketing officer says the change was a necessary
one because the brand name “YouSendIt” didn’t accurately describe the
company’s services anymore. “We’re moving away from a single-product company to
offer a multi-product suite,” says Trigg. Previously, YouSendIt was known as a
cloud-based service people used to send large files via email. Now, says Trigg,
the service offers shared storage folders with unlimited space options, syncing
capabilities across multiple devices, mobile apps and digital signature
services. The name change, along with additional services is being rolled out
gradually, with users first being informed via email and a series of
accompanying how-to videos to ease the transition.

The company worked with branding
agency Siegel + Gale  to come up with a
dozen new names, Trigg says “Hightail” tested the best out of all the options, as
it was a real word (as opposed to some of the more ridiculous made up words
some startups
are using) and it could also be used as a verb (as in “why don’t you Hightail that over to me.”)

The name was also chosen to
be deliberately ambiguous about the company’s services.  “We wanted to get away from names that were
overly descriptive of what we do,” says Trigg. “We wanted to make sure they didn’t
limit people’s perception of what we could offer.”

Trigg says the company also
tried to get away from the common cloud-storage words such as “box,” “share,”
“sync” or “store” since they were now so common, creating a very “homogenous
space” that they wanted to avoid. It’s a clear effort at differentiating itself from competitors Dropbox and Box, behind whom YouSendIt has trailed. It
currently has over 43 million users, compared to Dropbox’s 175 million and
while Box has fewer users, it has far more funding than YouSendIt, which is
currently not cash flow positive.

Another way YouSendIt is
differentiating itself is through its end users. Trigg says Dropbox has long
been the tool of choice for consumers while Box has always focused on
enterprise business. Hightail, he says will occupy the segment of “creative
professionals,” which is consumers who will use the Hightail platform for work.
“Tools like these get adopted by end users first,” says Trigg. “Our strategy is
to get them to adopt the software organically,” says Trigg. By marketing to the
end user, the company’s enterprise strategy is to have them create the demand
for it, rather than marketing to the IT department and having them impose the
software on the users.

It remains to be seen how
the company’s long time users will adapt to the name change, but Trigg says so
far feedback has been positive, and the change should be smooth. “There is
definitely a period where people will take some time to get over the shock,” he says. “But
we expect they’ll get used to it pretty quickly.”

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