YouSendIt

Hightail, formerly YouSendIt, raised $34 million. Here's why

November 19, 2013: 11:59 AM ET

We sit down with chief executive (and one-time "Peanut Butter Manifesto" author) Brad Garlinghouse.

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FORTUNE—Hightail, the file-sharing company formerly known as YouSendIt, has raised $34 million in new funding. The nine-year-old startup has been around much longer than newer entrants like Dropbox or Box, but recently it sought to revamp its image and differentiate its product features in order to stand out in an increasingly competitive market in which larger companies such as Google (GOOG), Salesforce (CRM) and Microsoft (MSFT) are also vying to meet users' file-sharing, collaboration and storage needs.

At the helm of the company's efforts to revive itself is newish CEO Brad Garlinghouse, a former Yahoo! (YHOO) exec who came on board about 18 months ago. Fortune caught up with Garlinghouse to find out more about his company's rebranding efforts, the competition and what he plans to do with $34 million.

Fortune: At what point will you stop referencing your former name, YouSendIt?

We will stop using it soon, probably by the end of the year. It's a balancing act. YouSendIt was so descriptive—to a fault. When we changed the name we were already offering e-signature and storage [features beyond file-sharing] and we had 43 million registered users. Our rebrand has far exceeded our expectations. We are moving on.

What other changes have you made since taking on the job?

Switching to unlimited storage [available through Hightail's Professional plan, for $15.99 per month] was a big change. E-sign is a capability that we continue to enhance. Control and tracking is an area we had but continue to invest in. In a crowded market, it's critical to differentiate. We also have new people on the team, including our new CFO. There are a bunch of new faces around here.

This is the first round of funding you've raised since taking on the CEO job. How will you use the money?

There was some money in the bank when I got here. This has been a frothy category, but we've tried to be very judicious in how we grow our business, and grow smartly relative to our revenue growth. It's been three years since we last raised money. We've doubled the size of our enterprise sales team in the last 90 days. Internationally we just recently started to invest and hired our first employees in Australia and the U.K. We also bought a small company called adeptCloud. And we are continuing with product differentiation. Western Digital Capital led this round, but all existing investors participated.

Dropbox recently announced a more integrated approach to accessing business and personal files. Is that something that could work for Hightail?

We have focused on the professional use case for many years. Like [Box CEO] Aaron Levie said, three years ago people talked about LinkedIn and Facebook competing with each other in the social networking space. Are they competitors? Sure, but they're different. We're going to focus on different aspects of how we go to market and different product features. For Dropbox to continue on the growth trajectory they seek they need to go upmarket, where we and Box have been.

What's next for Hightail? Now that you have a broader company name what other products or features will you add?

The number one thing you'll see more from us is making sure our products go beyond just storage—sharing with professional capabilities that our customers want. Security to an end user means control and it means tracking. Our most popular feature is "read receipt" [which shows users when a file has been downloaded by a recipient]. Also, to expire a file after download, or password protect a single file. There are all kinds of permissions like that.

I really do believe that people want their cake and they want to eat it, too. It used to be all of my data was on my laptop. Now I want it in the cloud—but I don't want to give up the control I had on my laptop.

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