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In 1987, Jackson began his professional career in transportation with Yellow Freight. From 1988 to 1991, he was employed by Star Leasing as a Sales Representative and rose to the position of Sales Manager. From November 1991 to November 1994, Jackson was employed by Penske Truck Leasing as a Lease Sales Representative. In December 1994, he returned to Star Leasing as Vice President of Sales and Marketing. In 1998, he was promoted to Senior Vice President of Marketing; and later to Executive Vice President and Chief Operations Officer in 2004 to reflect his increased leadership role within Star Leasing. Jackson was named President/Chief Executive Officer in 2012. In addition, Jackson serves as Chairman of the Board for Star Leasing’s Board of Directors. Jackson graduated from Ohio University in 1985 with a Bachelor of Science degree in Communications.