Chief Information Officer

The Hightail Culture: Why Does Hightail CEO Feel Culture Is More Than 'One Size Fits All'?

Brad Garlinghouse, CEO (SF) of Hightail discussed issues regarding file sharing, such as security and how disruptive technologies are affecting many industries.

Jason Redlus: Can you start by telling us a bit about your background and about Hightail?

Brad Garlinghouse: Hightail is a secure file-sharing and collaboration platform focused on professionals. We have more than 40 million registered users and several thousand very large corporate accounts ranging from the largest of the large, with our biggest deployment being 37,000 seats. We continue to focus on delivering security around control and tracking, and delivering across a breadth of integrations to other content repositories. I joined Hightail almost 18 months ago when it was called YouSendIt. I had a viewpoint that while we were known for send, there was much more that we could do, and we really outgrew our name in every way I can think of. So we went through a rebranding process almost exactly three months ago, and we continue to grow from there.

You’ve got such an innovative product and solution there, but how does Hightail use its own product?

We have hundreds of thousands of customers, and we do telephone support in our primary office here. When I first got here, I had every single employee sit in on a minimum of two hours of customer support calls and hear what people were saying; what they liked and what they didn’t like. That experience alone was really good for every employee, because whether you’re working the front desk or a designer, hearing firsthand how people use the product is a really important step.

Now inside Hightail, we use the service very aggressively, from our design group to frankly myself. I use Hightail for when people access content on the site; I can see that information, the metadata about who accessed it, when they accessed it, how often they accessed it. One of the things that’s nice for me is I use our service to share all our board information and minutes and any resolutions, those kinds of things. And I can see who on our board does their job and actually looks at the doc before they show up at the meeting. I think any time you’re managing your content, the more understanding you have about how the people with whom you’re sharing it are interacting with it, the smarter you’re going to be.

“I think culture is not one-size-fits-all. While I have all kinds of things that I try to do toward investing in culture, by no means do I think that they would work for every other organization.”

You have a large general counsel membership that deals with a lot of sensitive company information. What’s your approach towards security?

From the beginning of the company, YouSendIt took security very seriously. Data was encrypted in transit, and that continues to be the case, while we invested in things like step three compliance. We do a lot of customer research and we actually talked to different customers such as general counsel about security, because they talk about it in different ways. General counsel talk about it in the context of control, the ability to password-protect a single file, to expire a file after a single download, and to share files with a feature we have called Verified Recipient Identity that allows others to access information I have shared if they login and verify their identity. Those are the kinds of controls that are appropriate if you’re a general counsel or frankly anyone dealing with sensitive information, such as HR professionals. You want to make sure that you don’t lose control of that data and lose control of that content.

One of the big problems with Dropbox is you can share something with someone and then that person can share that same link, and you don’t know how widely it’s gotten out there and how frequently it’s being accessed and touched. All those types of things like your metadata on what you are sharing are very important when you’re talking about professional information.

I know that you are big when it comes to culture within an organization, so how do you lead your own organization?

First of all, I think culture is not one-size-fits-all. While I have all kinds of things that I try to do toward investing in culture, by no means do I think that they would work for every other organization. The recipe that’s appropriate for one organization and one group of people is sometimes different from another. That being said, one of the first things I did when I got to the company was invest in rewriting the core values of the company, which at the time were Customer, People, Results (CPR). To me, customers aren’t a value, people aren’t really a value and results aren’t really a value. Also, I felt that CPR was ironically not an appropriate acronym when you’re trying to get people excited about things. So I rewrote those with the first one about being passion, because so often when I’ve hired people, just screening for passion goes a long way. If you are incredibly enthusiastic and passionate about something, you’re much more likely to overcome other inadequacies.

The second one is being real and authentic. I’ve worked at large organizations in addition to smaller organizations, and one of the things that I feel happens over time is people get less and less authentic. You sit in a meeting and you feel like there’s politics going on. People aren’t saying what they really think because they’ve got some other agenda that they’re working on. I have found in my experience that more work gets done more quickly with more overall high moral when people are just being direct and honest with each other.

The third one is being bold and taking risk. As companies get bigger, they hire people whose job it is to mitigate and reduce risk, such as, with respect to them, general counsel and HR. I want to make sure that as we grow as a company, we continue to try to take lots of risks in how we operate, the products that we sell and how we hire. I think who you hire and fire tells more about your culture than anything else you do. And so we’ve tried to live those values in all aspects of what we do here, and I certainly think first and foremost you have to lead by example. So I try to be pretty passionate and pretty direct even when it involves difficult questions, and make sure that I take risks in my day-to-day activities.

“I think any time you’re managing your content, the more understanding you have about how the people with whom you’re sharing it are interacting with it, the smarter you’re going to be.”

You’re at the center of a lot of disruptive innovation. What is your company seeing or hearing regarding the growth of mobile and consumerization of technology?

I think there are pockets of this that all of the companies in this space are benefiting from. The explosion of tablets as a core way in which we manage and interact with our data has been a huge tailwind for us as a company and for the whole category, because all your information is trapped in your laptop. That’s a problem if I want to access it on my smartphone or iPad or whatever tablet, but it’s also an opportunity. How I see things evolving is that increasingly, you could see companies differentiating and creating either sometimes a vertical focus or sometimes a specific product functionality as differentiation.

In terms of where the market’s going in using agile and innovative ways of collaborating and sharing information securely, what inning do you think we are in when it comes to more companies adopting something like your product?

I think it is in the very early innings, while we will see this very strong tailwind continue in terms of interest in this space. Another element of why I think it’s in the early innings is actually reflected in some of our strategy and our tactics, because there are so many companies competing in this space. The Gartners and the IDCs have said they’ve seen 60 to 80 companies in this space, and I’m not surprised by that.


Brad Garlinghouse
Brad Garlinghouse is the Chief Executive Officer of Hightail, formerly YouSendIt, Inc., a file collaboration service for professionals, with a mission to give people the simplest and most secure way to share their content with anyone, anywhere.

Brad believes that a truly successful company begins with its employees and the culture they build together as a team. Great people build great products and great people gravitate towards great company cultures.

It’s a philosophy that Brad has cultivated throughout his career, from management stints at SBC Communications and @Home Network to his time as CEO of Dialpad Communications. As a Senior Vice-President at Yahoo!, Brad was responsible for all of the company’s communications products, including Yahoo Mail, Messenger, Flickr and the Homepage. His transformation of that group’s culture gave teams ownership of their products and encouraged experimentation that led to notable successes, including both Yahoo! Mail and Yahoo! Messenger becoming the clear leaders in their respective spaces.

Most recently, Brad was President of Consumer Applications at AOL where he transformed its Silicon Valley operations, expanding the reach of its existing products and reinvigorating mobile and social strategy.

Brad holds a BA in economics from the University of Kansas and an MBA from Harvard.

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