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Wingman Has Your Back

  • nigeledelshain
  • Nov 10, 2025
  • 5 min read

IN THE MILITARY, a wingman refers to the second aircraft in a flight formation. The lead aircraft is responsible for guiding the flight to accomplish the mission; the wingman’s job is to support the lead and have its back by doing everything possible to allow it to focus on completing the task.


It’s in this spirit that United States Marine Corps veterans and brothers Jay and John Neagle named their venture, Wingman Business Solutions, which aims to bring the integrity and commitment of the Marine Corps to the merchant services industry.


Simply put, the merchant services industry refers to the businesses and technologies that help merchants accept and process payments, especially via credit and debit card transactions (think the machines that you tap your card on to pay just about anywhere these days).


It’s an industry that’s not only extremely saturated, according to John and Jay, but they also say it gets a bad rap due to lack of transparency and poor customer service.


The brothers saw the need for forthrightness and connection to clients in the industry—they say it’s what sets Wingman apart.


“Wingman will be present to shake your hand, thank you for your business and address questions and issues right when they arise, for as long as needed,” Jay says. “Let your problems become our problems.”

 

MARINE CORPS VALUES

Before Wingman was founded in 2022, John and Jay each spent time in the Marine Corps.

Jay was motivated to join after 9/11.

 

He was a junior in college at Villanova University when the planes hit the World Trade Center and was deeply impacted.


He applied and was accepted to the Marine Corps Officer Candidates School. Attendees go to “leadership boot camp” in Quantico, Virginia, to experience military life but are not committed to the service. Jay went for 10 weeks after his junior year and says it was an amazing experience, during which he learned a lot about himself and his body’s capabilities, both physically and mentally. He then returned to Villanova for his senior year and went on a couple of job interviews after graduating but was uninspired.


“I realized sitting behind a desk wasn’t for me—I decided I would serve my country,” he says.


Jay gained experience solving complex problems and leading large teams as a Lt. Col. and helicopter pilot. He did four deployments overseas, two in Iraq, two off a boat in the Mediterranean Sea, and lived with his family in many different locations including for three years in Australia.


He found his experience serving so valuable that he convinced John, who is 10 years his junior, to try Officer Candidates School. John applied and attended the program for six weeks after both his junior and senior years.

 

John, who lives in Ho-Ho-Kus with his wife Erin and their three children, says he hadn’t thought seriously about joining the Marines up until that point. But he loved the training and decided he would do a four-year minimum contract after graduating from the College of New Jersey.


“We were raised in a household that believes in service; we went on mission trips with the church growing up and we believed in giving back,” John says. “We also had a profound sense of patriotism in our house.”


John was a Marine Corps Logistics Officer. He planned and executed the movement and maintenance of Marine personnel and equipment to support combat operations, as both a tactical convoy commander and an operations director. He had one deployment overseas in the Middle East.


“That’s what the Marine Corps does to you; John was 24 years old and responsible for, like, 100 vehicles, 200 people, and moving equipment through a warzone,” Jay says. “There’s a huge amount of pressure and responsibility involved and that comes with huge accomplishments.”


John says that’s why they are so successful at what they do now.


“We take all that energy and put it into finding the right point of sale system at a restaurant,” he says. “Building a relationship with our clients is extremely important to us.”

 

‘NO LIMIT’

When Jay retired after 20 years in the Marine Corps and settled with his wife and three kids in Robbinsville, he wondered what was next for him professionally. His and John’s father,

Bob, has been in the equipment leasing industry and lending arena for the past 40 years, leasing everything from airplanes to cranes to restaurants.


But for the past 20 years, his focus has been on the point of sale industry, leasing equipment you see for transactions in restaurants. He had formed relationships with many merchant service providers and understood the data behind the hardware.


Their father’s experience and connections helped John and Jay understand that there was a hole in the market that they could fill, and Wingman Business Solutions was born. Bob serves as a lending specialist and executive consultant for Wingman. His sons say he’s “full of wisdom and a great resource” for them.


“Business owners get frustrated: Rates increase over time and customer service drops off or there’s a new agent all the time and they are never able to build a relationship,” John says. “Many merchants crave that relationship and knowing that someone will come and physically help them and answer the phone when they’re in crisis.”


John says he recalls seeing on social media one night that Restaurant A in Ho-Ho-Kus, formerly Albert’s, was unable to take credit card payments because their system went down. He knew if they oversaw the restaurant’s payments at the time, Wingman would commit to fixing the problem quickly and efficiently.


“This equipment can be a major headache,” he says. “If you’ve got a dinner rush and you can’t take payments, that’s a huge problem. To be able to put somebody at ease so they know they don’t have to worry about that, and they can focus on their passion, their business, is really rewarding.”


The brothers say it took time and patience to form a trusted relationship, but Restaurant A is now their client—and if their system goes down, Wingman can have another one programmed and brought in within half an hour, they say.


Besides stellar customer service, John and Jay say what helps them stand out is they work with dozens of point of sale systems and online gateways so they can find the right fit for each business. Many times, agents only work with one service (some examples of different systems include Clover, Toast, and Square).


“We don’t want their business to conform to our product,” John says. “We want to conform to their business.”


Jay says the dedication to finding the right fit comes back to their Marine Corps values.


“We learned in the Marines that you accomplish the mission—it’s no fail, you figure it out,” he says. “We put the time and effort into figuring out what the right product is. Sometimes it’s easy, sometimes it’s more complicated.”


Wingman has about 100 clients right now, from Connecticut down to Georgia, with plans to expand. There’s “no limit,” John says.


The pair loves working with family and that includes other military veterans; John and Jay feel Wingman offers them an inspiring place to land after serving.


“They understand that we’re aiming to accomplish a mission and the commitment to seeing it through to the end,” Jay says. “The integrity and all the things we espouse, all of our values are shared.”


BY SARAH NOLAN

 
 
 

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