Third generation is gradually taking over family-owned business started in Oswego in 1976 — new 30-year business plan includes opening additional 29 offices throughout the Northeast
By Tom and Jerry Caraccioli
When Lou Usherwood decided to buy the family business from his parents in 1997, he set goals for how he wanted to grow the business.
What started as a business being operated from the first floor of the family’s home, a converted convent on West Erie Street across from the former St. John’s Catholic Church in Oswego, has grown to 19 offices throughout the Northeast, including 10 in New York state (Syracuse, Albany, Buffalo, Rochester, Binghamton, Utica, Watertown, Jamestown, Plattsburgh and Potsdam), four in Massachusetts (Boston, Springfield, Auburn and Plymouth), two in New Hampshire (Manchester and West Lebanon), one in Connecticut (Hartford), one in Vermont (Burlington) and one in Rhode Island (Providence), 176 employees, more than 4,000 clients and a yearly gross revenue in 2025 of $50 million in sales.
It is safe to say Usherwood has more than eclipsed the first goal he set for the business. And today, the chief executive officer of Usherwood Office Technology and his team are celebrating the company’s 50th anniversary.
“In 1997, I purchased the business from my parents,” said Lou, the youngest of the four children of Charlie Sr. and Carol Usherwood. “I was 33 years old and I had an expansionist slogan I came up with — ‘Statewide by 2005.’ When I held company meetings I would say, ‘We’re going to be statewide by 2005.’”
While it took him and his team a few more years than originally planned, Usherwood grew to reach that goal and beyond.
Usherwood Office Technology grew from humble beginnings. Charlie Sr. and Carol had started their entrepreneurial journey in 1964 partnering with Jack and Donna Hammill to form Ontario Business Machines. In 1976, the Usherwoods splintered away from OBM and created Usherwood Business Equipment.
“When I think of my mom and dad, you have an offense, my dad, and a defense, my mom,” Usherwood said. “My dad’s best attribute was curiosity. But there had to be someone to keep that curiosity within the boundaries that would work. My mother was that person.”
By 1979, growth allowed the Usherwoods to expand to downtown Oswego where they established an office on West First Street. They had eight employees in 1980 and in 1981 became one of the first companies in the U.S. to sell and service both copiers, duplicators, typewriters and mimeographs. This unnamed element of business at the time would become known in today’s business vernacular as a managed network service group.
“In the old days we might sell you a typewriter or copier and then go fix them,” the current CEO explained. “As business progressed in office technology, there have been very few people who can service all of it. And there’s very few people who can proactively come in providing solutions that are scalable.”
When Usherwood Business Technology comes in with a managed network plan for a business, they take work away from the client and explain they don’t need to hire IT people. Usherwood Office Technology manages everything — cyber security, firewalls, servers, all the company’s PCs, multifunctional copiers, printers and any other technology, including video technology and surveillance cameras, as well as phone systems.
“Ideally, our clients can rely on one partner to supply the types of services that are considered as good as it gets for service and quick resolution,” Usherwood said.
Family affair
The path to today’s current business plan continued to grow in 1981 when Charlie Usherwood Jr. joined his parents. Charlie Jr. graduated high school in 1981 and went right into the business at the start of the personal computer origins, when Steve Jobs and Bill Gates were just beginning to reshape the way the world communicates.
“It was the first time in my life that I was faster than anybody else,” Charlie Jr. said. “I realized I was going to be in the computer business the rest of my life.”
Charlie Jr. left the company in 1988 and moved to Buffalo to work in IT. In 1997, when youngest brother Lou bought the company from his parents, the first call he made was to his big brother, Charlie Jr., to rejoin the company as the chief technology officer because he recognized the future of the company would be in IT. It wouldn’t be the first time the CEO would recognize a potential trend before it occurred.
“The decade between 2003 and 2013 was the renaissance of Usherwood Business,” Lou said.
A new logo and branding, office expansions and the proliferation of new employees began to build. Soon after, Usherwood Office Technology experienced a ubiquity that stands today. Authorized partnerships with Sharp, Canon and Ricoh through the years lifted the Usherwood name statewide by 2008. Plans involving video conferencing — before 2020 and the COVID-19 epidemic — also enabled Usherwood to gain a valuable advantage in its business.
“It was where we laid all the foundation to actually create something that was long lasting,” Charlie Jr. explained.
In 2013, Usherwood Office Technology was recognized by the now-defunct CNY Business Journal as one of the best places to work in Syracuse. The brothers took note that this recognition was evidence their employees liked where they worked and coming to the office every morning.
“There was no higher honor to a business owner than a compliment like that,” Lou proudly said.
And that evidence is clear today when Usherwood employees — noted as team members throughout the business — talk about their experience working for this 50-year-old company. “We really care about each other, the way we treat each other, the way we work together,” Briana George, a 10-year member, said.
Take careful note of the designation “team member.” It’s not by accident. It is inherently built into Usherwood family DNA.
As a standout all-state hockey player growing up in Oswego, Lou Usherwood was no stranger to setting goals and working to accomplish them. With that experience playing team sports, most popularly and notably hockey, the Usherwood brothers and family treat each other like team members instead of just employees.
“The one cultural component that is part of today and has stayed from the very beginning is family,” Charlie Jr. said.
These days Usherwood Office Technology is ubiquitous throughout the region.
Its current impetus for future growth is built through a recent 30-year business plan that includes opening 29 offices throughout the Northeast. “I have three children that were interested in coming into the business,” Lou explained. “Had I not had their interest, more than likely I wouldn’t have had the creativity to do what I ended up doing.
“For our business, managed IT is the fastest growing part. It is also the most complex business line that we carry and it is growing rapidly. The print and multifunctional copier business is considered ‘mature’ as of 2017. That means it’s not growing. For us, it’s still growing because we’ve taken on all of New England and we’re getting new customers and market share.”
Usherwood also picked up an additional line of business as one of the first dealers in the business industry for security and surveillance. This double-digit growth emerging market became an additional line of business that complements the company’s prescient video conferencing systems established in 2017.
While Lou is convinced his parents — both deceased — are looking down at their family with smiles, the next generation of Usherwoods, daughters Lindsay, Lauren and Leslie, are picking up where their grandparents, father and uncle have left off.
“The mission for the third generation is to execute on what the first and second generations have already built,” the company’s general counsel, Lindsay Usherwood, said. “That is to continue to deliver world-class services to our clients.”
Tom and Jerry Caraccioli are freelance writers, originally from Oswego, who have co-authored three books about hockey. They also host a monthly television and multi-platform segment on WSYR-Channel 9 (ABC) – “Backroads to Bridge Street with Tom & Jerry.”
