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“Risks come in steady, escalating steps that ask you whether you want to fold or double down.”

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As chief strategy officer of Bomgar, Nathan McNeill is responsible for aligning product strategy with the needs of more than 6,500 Bomgar customers. Nathan functions as a product evangelist, and speaks frequently at technology conferences, industry events, and customer and press engagements. He also helps establish and maintain technology partnerships and is instrumental in expanding Bomgar’s customer base. McNeill joined Bomgar as a co-founder in 2003, while attending Belhaven College, where he graduated with a bachelor’s degree in philosophy.

Bomgar provides remote support solutions for easily and securely supporting computing systems and mobile devices. The company’s appliance-based products help organizations improve tech support efficiency and performance by enabling them to securely support nearly any device or system, anywhere in the world — including Windows, Mac, Linux, iOS, Android, BlackBerry and more.

MO: I’d love to hear how you became the chief strategy officer of a software company with a bachelor’s degree in philosophy.

Nathan: I knew a guy. Joel and I were friends all the way through college and used to study together for many of our classes. A couple of months into starting Bomgar, Joel realized he needed someone who could repeat a few technical phrases for sales calls and work for peanuts. I wasn’t at the top of that list, but Patrick Norman (who joined us a couple of months later) refused initially and I sneaked in. Of course, once you get involved in a startup, you fill a lot of different roles along with what you were hired to do, and I’ve gotten to do pretty much everything at Bomgar except the really important stuff (programming and accounting), because they were afraid I’d mess them up. In actuality, though, I think that many more liberal arts majors should get involved in business and technology. Businesses are filled with left-brained, analytical sorts and they need balance. It helps to be able to take a more philosophical approach to business strategy. Philosophy is about concepts (sometimes very abstract concepts) that people have tried to build the world around. Or vice versa, sometimes people have started with the world and tried to build the concept based on what they see. No matter which direction you take, it’s not too different than what occurs in business. Sometimes you assemble the facts and try to build a cohesive concept from empirical evidence, and sometimes you start with an idea and try and see if you can shape the market to meet that idea.

MO: What kind of products or services does Bomgar offer and who is your target audience?

Nathan: Bomgar offers a remote support appliance that we sell to technology support centers; both internal service desk and external customer tech support organizations. We generally sell to larger companies, but have customers of all sizes. Our customers tend to have a very heterogeneous technology landscape—meaning they support lots of different types of systems and devices—and are typically very security conscious. Our appliance-based model means that when you remotely access an end-user’s screen and walk them through a problem, the data never passes through a third party. Everything is securely routed and auditable through the appliance, which is inside our customer’s firewall.

MO: How have you been quickly adjusting and leading the way in remote support for mobile devices? Have you had to pivot your business model to do this?

Nathan: The developments in mobile devices over the last ten years have been truly stunning. I feel really blessed to have begun my career right as the internet was hitting its stride and virtualization and mobility were combining efforts to redraw the technology’s boundaries. In some ways, everything is completely different. When we started in 2003, the cutting edge was the Palm Treo 600. No one would have thought to remotely support it. For one, only a few Uber-geeks had it and second, all they could really do with it was look at their calendar and send email. Now, it’s getting harder and harder to figure out whether a smartphone is a small computer or a computer is a large smartphone. The first mobile devices didn’t even register on tech support’s radar but the new ones, especially tablets, are forcing support to expand their skillset by double or even triple.

Keeping up with this shift has meant a lot of work on our product to ensure that it’s compatible with all the latest technology. We haven’t had to do an about face, because the process of providing support hasn’t changed as much as what is supported, but if you look at our code base, our product from only a few years back would be next to useless. You don’t often think about support technologies being on the cutting edge, but in the case of our product, if we aren’t on the cutting edge then our customers are on the bleeding edge.

MO: I love that you mentioned winning a major account from a competitor in 2009 after losing the initial bid to the same competitor in 2004 when you were just getting started, as a major company accomplishment. How do you think that Bomgar has evolved and improved since first launching?

Nathan: It’s sort of like growing up. About half of growing up is figuring out what you’re really not good at no matter how hard you try, and the other half is figuring out how to make what you’re pretty good at really great. We’ve made enough mistakes to fill a book, but that process has given us firm convictions about the areas where we think we have winning capabilities. This sharpens our focus and allows us to move on from ideas that may be good, but only for some other company.

Self-knowledge is as critical for a company as it is for an individual. We chose the appliance model a long time ago, and we’ve realized more and more over time just how critical that has been to our company’s success. It’s allowed us to hone the security of our product, it’s kept us out of the bloody battle between our SaaS competitors, and it’s allowed us to keep our product simple even as we support a bunch of complex “stuff.”

Our capabilities in screen sharing technologies have come a long way as well. At this point, there are only a couple of other companies in the world who have a similar level of expertise. The combination of the appliance model and our long-term focus on screen sharing has enabled us to fill a market niche for secure remote support better than anyone else out there.

MO: What’s the biggest risk that you’ve ever taken and how did it turn out?

Nathan: All of the biggest risks we took as a company happened before we realized how fast we were driving. At one point early on, before we brought on outside capital, we had about two weeks’ worth of cash in the bank. We hit the phones, cranked back on expenses, and the crisis passed, but at the time, it was just par for the course. . . sort of like the fourteen-year-old skateboarder you see pick up after a crash and say “that was awesome.” If he was forty, he wouldn’t say that.

Even so, it’s hard to pinpoint one single biggest risk. I think that’s a misconception. Risks come in steady, escalating steps that ask you whether you want to fold or double down. The success of our company has come from continuing to double down and take the next step until the success of the last step makes the next a little less risky. Early on, every step could have been our last. Now, we can afford a couple of mistakes. The challenge we have going forward is how to keep the self-preservation instinct from stealing from our future growth. The ironic thing is that it’s easier to take risks earlier on when you have everything to lose than when you’re big enough to absorb a few body blows. There’s a certain amount of ignorance, I think, that’s required to take the risk of starting a company.

MO: How does it feel to be a part of the technology revolution? How do you see your industry changing over the next few years?

Nathan: You know, it’s sort of like watching your kid grow up. From outside the industry, it must seem like things move startlingly fast, but from the inside—with rare exceptions—things seem to move very gradually. In the long term in technology, things always change way more than we expect. Who would have predicted in 1995 that Apple would be twice as big as Microsoft by now and would have gotten their by creating such stunning devices? On the other hand, in the short term, technology moves much slower than we expect. It’s funny to me how industry analysts make predictions like “by 2014, everyone will use thin clients.” Their thinking is that two years is like an eternity in technology and surely after 24 whole months, everything will have changed.

So I try not to make too many embarrassing predictions about future scenarios that I’m sure to miss on one side of the mark or the other.

However…I think that there are a couple of resilient trends that will stand the test of time. I think that mobile devices will continue to expand in capabilities and I do think that, over time, our concept of a “desktop” will come to refer to more of a synced environment vs. just a particular device. However, I don’t think (as many technologies have tried to do over time) that the user’s operating environment will be the same on every device. I think that the individual services will share common threads to aid in familiarity, but I think that the form factor of the device will dictate how the matrix of services is interpreted for the user.

Also, I think that security is only going to become more critical over time. To some extent, personal privacy has already been destroyed by social networking, but there is still a lot of confidential information that must be safeguarded. The old data warehouse guarded by three Doberman Pinchers approach doesn’t work anymore, as Wikileaks has taught us. The fact of the matter is that almost all information worth stealing is now connected to the internet somehow, and security officers are in for a real challenge in figuring out how to logically segment this open and connected world into a framework that is both flexible and resilient. You want universal information accessibility but only for a limited universe of users.

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