Balancing Business, People and Technology

Bringing best practice technology solutions to diverse customers


Jay Strickland is the President and CEO of WingSwept, a technology consulting firm whose mission is to help clients leverage technology in order to achieve better results in their organizations.

WingSwept’s clients range from small businesses with one or two employees, to federal government and Fortune 500 level companies. Their work covers a broad spectrum and is divided into four divisions: Government Services, Network Support, Web Development and Vertical Marketing.

WingSwept had its humble beginnings in 1995 when Strickland was attending college and doing consulting for a few clients on the side. After completing the ROTC program at N.C. State, he went into the Air Force and maintained his existing consulting clients. Strickland was later made captain in the Air Force and made the decision to leave and pursue his work with WingSwept full-time in 2002.

He says he never really started out with the notion to build a business, but things fell into line over time to make that a reality. WingSwept has adapted and thrived off the dynamics of technology for the past ten years. Technology has allowed WingSwept the opportunities to enter new markets and to provide targeted technology offerings for each diverse customer base.

“Web Development was once the only source of revenue for WingSwept, but is now the smallest part of our organization,” says Strickland. “I appreciate our foundation in Web Development, but diversifying our revenue and having a broad range of customers in four different divisions is what has set us apart.”

The type of work that WingSwept does is varied and based on division. The company’s Network Division typically deals with local small and medium-sized businesses that need help managing servers, computers and firewalls. Strickland explains that WingSwept focuses on first laying a foundation of trust with its customers.

“Both trust and security are critical for a business and its IT provider,” Strickland explains. “Like our customers, we are a growing business, which is why we know how to customize secure technology solutions that fertilize growth and success.”

“For our Vertical Markets division, clients fall into one of our three verticals, which are automobile repair, collision repair and HVAC service,” says Strickland. “In that division we sell affordable websites specifically to those verticals. We have almost two thousand clients in all fifty states in that division.”

In WingSwept’s Government Division, Strickland has been able to parlay his military experience and reputation into work with the U.S. Intelligence Community on various projects dealing with national security issues. His company has provided high-end technology consulting to military, government and prime contractor clientele on enterprise projects.

Today, WingSwept’s government division focuses on selling software to inspector general clients at the federal, state, and local level.

Regardless of the division, Strickland has the same standards for treating all his clientele.

“Respect, loyalty, trust and integrity are our core values,” he says. “Our mission statement is to help our customers leverage technology in order to achieve better results. And in terms of how we get there, we want to be profitable and have fun.”

Treating his employees well is very important to Strickland. He has created an environment where people want to come to work, where they feel valued, and where they know that if they perform they will be rewarded.

“We believe a lot in incentivizing people and aligning goals,” Strickland explains. “We implemented a performance pay system nineteen months ago. All of our folks receive bonuses based on bottom line results. As a result, we’re getting ready to post our twentieth straight month of profitability through a recession. We’re proud of that. We pay our employees bonuses on that program every single month.”

Additionally, Strickland is sensitive to the fact that in today’s economy, new hires may be coming from a background of extended unemployment.

“Financial crisis in your life leads to all sorts of personal crisis in your life, and you can’t just dig out of that very fast,” he relates. “So that’s probably one of the things that is unique to this period in our business. It’s kind of helping out those employees and figuring out how can we help them get back on level footing.”

To assist with this process, WingSwept facilitates its employees completing Financial Peace University, a program designed by Dave Ramsey to help people eliminate debt and save for the future.

“Most of our employees have taken that course now,” says Strickland. “The company pays for the cost. We provide the meeting space, the snacks, and if the employee needs child care, we provide that too.”

Strickland’s advice for other business owners and entrepreneurs is to learn the fundamentals, something that he’s observed as being overlooked at times.

“In my perspective, when someone doesn’t look beyond the balance of their checkbook and understand business trends and fundamentals, they risk overleveraging themselves,” he says. “I know as a business owner, usually the hardest part is knowing when to ask for help, which is why I recommend establishing close relationships with business owners in and out of your industry.  You never know what you will learn from each other.”

WingSwept has grown over the years, and Strickland says that this increase in scale has allowed the company to offer unique services, while mitigating risk.

“For the first two years, in our Vertical Markets division, we lost money knowing that in order to make money, we had to break past a certain threshold number of customers,” he explains. “And then at the point that we got that, we could do things like give unlimited support calls at no additional charge because we would have the money to fund having the customer service staff ready and waiting for customer requests. Once we have scale in place, then we can sell a product cheaper than competitors have the technology in place to build the product.

WingSwept is poised for more growth in the future. The company has recently added another 4,000 square feet of space to their office site in preparation for this potential. Like many things in his career however, Strickland says he could not have predicted this path.

“We don’t look at growth for the sake of growth,” he explains. “We bought our first office space in 2004. And somebody asked me when we bought it how big I wanted to grow the company. So at that time I said, ‘You know, if we ever get to twenty-five employees, I’ll consider that a huge success.’ I figured that would happen about the time I was 50 or 55, not mid-30’s. We’re at twenty-seven today, with expectations to be above thirty by the end of the year.”

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