President, AGIL IT

Wes Gipe

The Problem


Wes Gipe began working with Aileron late in 2008. At the time, his IT firm—Agil IT, pronounced agility—was growing rapidly. But the movement was happening through brute force. At the end of the day, his people were worn out, and so was he.

Wes was 19 years old when he launched his company with a $500 investment. He wanted to be a physician, so the idea was to save money for medical school. But someone, somewhere had other ideas. Agil IT quickly began growing at a 60- to 80-percent annual clip, with one year of 146-percent growth. Wes laughs about it now, but he’s not joking when he says he doesn’t care if he never experiences another year like that again. “Anything anyone wanted, we told them, ‘Sure, yeah, of course we can do that,’” Wes says. “We ate what we killed, and we killed anything that moved.” It’s the way many businesses start. Wes and his team were generalists in a general market. They lacked focus. He was managing by trial and error. He realized the company needed operational help, so he hired a president to run the business. The arrangement lasted three years, and it was a learning experience.

The Solution


In December 2008, Wes resumed leadership of the company. A friend suggested that he take a serious look at Aileron. He was skeptical, he admits now, basically out of a misunderstanding of how strategy and vision can propel a company forward. Then he took the Course for Presidents and brought his senior managers to Aileron, too. After a meeting with Aileron Consultant Bill Matthews, his opinion changed. He remembers Bill asking good, provocative questions— questions that made him think. “It became apparent that the true desire of everyone I met on the campus was to help me,” Wes says. “I learned, too, that as a non-profit, Aileron has no revenue to protect. That puts everyone on campus in the unique position of being able to be brutally honest. It was always quite apparent they didn’t need me, which is a cool position for a consultant to be in. All the consultants I’d worked with before had revenue streams to protect—they would be honest with me to a point, but their honesty only went so far if it meant it might interrupt that stream.” In the process of developing a strategic plan with Bill and another Aileron consultant, it became clear to Wes that changes had to be made.


First, there was the issue of focus. Working with Aileron consultants, the Agil IT team was able to identify its area of excellence. The team learned it had a definite affinity for delivering IT to the healthcare industry and in particular, to ambulatory physician groups. The new focus meant Agil IT had to part ways with some big-name national accounts, including one with a presence in every supermarket in the country. But for the sake of the company’s clarity of purpose, it had to be done. Agil IT became clearly focused, and the big-name client respected Wes’ team for it. “The move toward a strategic plan also allowed us to market our products differently. We sell hardware and software. But really, we’re a services company. That focus allowed us to market our service as purpose-built—specifically to that ambulatory physician market. So the conversations on the business development side have just gotten easier and easier because we now have a service that’s laser-focused on a specific market.”


Through Aileron, Wes also learned to give his people the freedom to make mistakes—to fail, because that’s how learning happens. The changes Wes had to make were easier than he anticipated because through Aileron, he had a new clarity of purpose. Some of the changes required Wes to let go, trust his people, and let them do their jobs. “You have to let people make mistakes,” he says, “even when it costs money, time, or a client. You have to, because it makes the organization get better,” Wes says. “We realized we weren’t good about discussing failure publicly in a positive way. Every organization fails on many levels. But with the help of the Aileron consultants, we developed a plan for presenting issues and analyzing them in a constructive manner, together as a group. So we were able collectively to stop certain failures from happening—and plug the holes that made those failures possible. Now it’s an expectation. When we do well, everyone knows we’ll dissect those successes publicly to identify what we’re doing right, and conversely, when we fail, everyone knows we’ll also dissect that publicly. That whole process has been extremely helpful.” Wes says his connection with Aileron has resulted in a 180-degree difference in the way he works and how his business functions. He no longer thinks just about today. He spends more time looking down the road, thinking about what’s beyond the next bend.

...the conversations on the business development side have just gotten easier and easier because we now have a service that’s laser-focused on a specific market.

The Results


He was surprised to discover that, as a result, he was becoming increasingly less busy. He says the defining moment came when he returned home from a two-week vacation. The second day back, in the middle of a Tuesday afternoon, he realized he didn’t have anything to do. For 15 minutes, he went into panic mode. “In the past, if I ran out of stuff to do, it meant we as a company didn’t have anything to do,” Wes says. “Then I realized I didn’t have anything to do because I had the right people with the right training all pointed in the right direction. They had gotten it done for me. I had learned to get out of their way and let them do it for me.” A year after beginning his relationship with Aileron, Wes knew it was working when he began hearing comments from employees’ spouses. Their husbands and wives were coming home from work less stressed and more excited about their work. Then he started hearing his people whistling on their way to work, and on their way home, after 12-hour days. “We don’t work any less diligently than we did before our relationship with Aileron, but we work so much smarter,” Wes says. “I expect us to do the same amount of business this year with significantly fewer people, and everybody’s happy about it.”


“The single best thing I’ve gotten from Aileron is time—and I mean time from a leadership perspective—time to think about what we’ll be like in three years, in five years, and figure out how we’ll get that done. Before, I had too much work to even think about strategy. Now, strategy is my work. I was in charge of a company I didn’t know how to run. It was to the point that my wife sat me down and told me I had a choice. I could slow down, regain control, and spend the majority of my time with my family—or I could sell. Because of Aileron, I was able to keep the company and make the choice I had to make for my family. For me, Aileron has been and continues to be a slam-dunk.” During a February 2009 meeting with his team on the Aileron campus, Wes decided to dispense with traditional titles and let his people make up their own handles. For himself, he chose Voodoo Guru and Fearless Leader, based on his observation that most people tend to think of IT as mystical and complex. “We were laughing, carrying on, and making a ruckus when in pops Les Banwart, vice chairman of Aileron’s board of directors,” Wes says. “At the time, I had no idea whether Les had a sense of humor or not. And I thought, ‘Here goes—we’re going to get ourselves thrown out of here.’” Wes explained to Les what was happening. Les grinned. “I knew our new culture was starting to take root when Les told us, ‘You guys look like a group of people who really enjoy being together. I’d say you’re going to go far.’ It meant a lot to all of us.”


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