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Fleet Advantage Names Next CEO
Fleet Advantage announced that its Chief Executive Officer, John Flynn, has retired effective December 31, 2022. Brian Holland, president and CFO has been named as the next CEO.

Brian Holland is the next CEO of Fleet Advantage.
Photo: Work Truck/Fleet Advantage
Fleet Advantage, a provider of truck equipment financing, fleet maintenance and fuel analytics, and lifecycle cost management, announced that its Chief Executive Officer, John Flynn, a 40-year veteran of the trucking and transportation industries, has retired effective December 31, 2022. Brian Holland, president and CFO has been named as the next CEO.
The move was part of a long-standing succession plan, which began in early 2021 with the formation of a six-member Senior Leadership Team, to provide day-to-day management and oversight of the business to continue its growth and prosperity.
Who is John Flynn?
In the 1980’s, Flynn founded his first startup which was to design and implement a nationwide lease program using highly structured tax leveraged lease financing for over-the-road semi-trucks and trailers. Later, according to Fleet Advantage, he pioneered the use of like-kind exchange (Section 1031 exchange), a tax provision that enhanced the lease economics. Since 1980, tax leveraged leases have expanded exponentially and now represent the largest segment of net finance leasing for new semi-trucks in the U.S.
During the early period of his career, Flynn decided to focus on private corporate truck fleets. He developed mathematical formulas to confirm that shorter lease terms resulted in lower total cost and also structured off-balance sheet operating leases. That philosophy served him well and in 2008 when he organized Fleet Advantage and added environmental stewardship to their services.
“We set out to build a company that would offer the flexibility but not the risk of ownership and combined the attributes of hard work and dedication and a commitment to excellence in customer service, using an innovative approach supported by data analytics to effect change within the transportation sector,” Flynn said. “We are proud of what our team has accomplished through the years, and are gratified to be serving a number of world-class private fleets that have adopted our philosophy and approach by focusing on asset management, including equipment acquisition, financing, fleet services support, and asset disposition and the total cost of ownership.”
Fleet Advantage introduced its first emissions scorecard in 2010 using data analytics and an innovative replacement program with flexible lease financing. Its (EXchangeIT) product was designed to allow companies to lease for shorter lease terms and take advantage of reduced life cycles and the upcoming wave of clean-diesel technology improvements in MPG and reduced maintenance. Their focus on fuel economy was visionary while also placing a priority on protecting drivers and motorists applying innovative safety features which, at times, included safety options added to equipment at no cost to their customer(s).
Flynn’s overarching vision of asset management helped the country’s top 100 private and corporate fleets reach Emission Reduction Goals (ESG) to promote sustainability. Today, under Flynn’s leadership, companies have vastly improved their environmental footprint by reducing CO2 emissions by over 1,000,000 metric tons. The company has purchased, financed, managed, and disposed of over 30,000 Class 8 vehicles with a current fleet size over 14,000.
“John has been a legend in the industry,” Holland said. “He’s helped Fleet Advantage earn the respect of both transportation and equipment finance industries, and his bold nature has been exactly what our nation has needed to constantly push the envelope to develop a cleaner, more modern truck transport system.”
Who is Brian Holland?
Holland joined Fleet Advantage in 2011 and was named president and a director of the company in 2014. He will succeed Flynn as CEO.
“I am incredibly honored and humbled to lead such a talented group of professionals into the future,” Holland said. “It is a privilege to carry on John’s legacy of delivering value and innovative solutions to our clients, providing ongoing career opportunities for our associates, and being a charitable member of our community.”
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