Meet the Sales Team

Our sales team has the depth of experience needed to execute tailored deals in support of a multitude of financing scenarios. Our relationships with direct borrowers, financial sponsors and business advisors allow us the ability to understand varying and dynamic needs for lending creativity and deliver certainty of close.

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Direct: 224.235.4551
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Anthony Di Chiara

EVP, Head of Sales

Anthony and his team are fresh faces in the lower middle market independent finance world, where they use a relationship-oriented approach to creatively structure asset based credit facilities for companies with up to $100 million in revenue. Anthony’s background comprises extensive experience at leading banks and finance companies including Wachovia Capital Finance, Merrill Lynch Capital, Heller Financial and Fleet Capital Corp., among others. He is active in the Commercial Finance Association, Turnaround Management Association, Association of Merger and Acquisition Advisors and Association for Corporate Growth. When Anthony is not growing Gibraltar’s business, he enjoys spending time with his wife and three children, staying fit as an avid runner and following alma mater Notre Dame on the football field and hardcourt.

Direct: 980.244.1376
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Mike Conrad

SVP, Southeast Region

Mike joined Gibraltar to open up the Charlotte office, where he is responsible for originating and executing new loan relationships in the Southeast region. His is also focused on developing ongoing value-added relationships with restructuring advisors, investment bankers, private equity groups and other transaction-oriented professionals in his region. Prior to Gibraltar, Mike spent nearly 25 years in various originations roles with companies including Wells Fargo and Bank of America’s asset based financing and corporate investment banking groups. At Wells, he was instrumental in developing the private equity asset based direct originations effort. Mike and his wife have two sons. His family enjoys tennis, running, cooking and traveling. Mike graduated from Wake Forest and enjoys following Deacon sports and attending Carolina Panthers games.

Direct: 310.921.9190
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Scott Shapiro

SVP, West Region

In representing the West region for Gibraltar, Scott approaches every commercial financing request by first listening to his client’s needs and then structuring a credit facility accordingly. He brings over 15 years of commercial finance experience to his role, having worked at both privately held and bank owned commercial finance companies. Scott is active in the local chapters of the Risk Management Association and a former board member of the Los Angeles chapter. He graduated from the University of California at Santa Barbara and currently resides in Redondo Beach with his wife and two children. When not helping clients with financing, Scott enjoys playing golf and beach volleyball.

Direct: 551.206.4767
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Elijah Kaplan

SVP, Northeast Region

Having spent over 16 years in direct lending, private equity investing and restructuring advisory focused on lower middle market and middle market companies, Elijah’s broad background allows him to understand borrowers’ needs and tailor best-fit financing solutions. Prior to joining Gibraltar, Elijah honed his collaborative approach to working with management teams and private equity sponsors while at DeloitteCRG, Hudson Capital Partners, Marathon Asset Management and Albion Investors. Elijah is an active member of TMA and ACG. Living in New Jersey with his wife and three children, Elijah considers his greatest accomplishment to be raising three loyal Denver Broncos fans in the New York area.

Direct: 214.347.0600
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S. Scott Simmons

SVP, Southwest Region

Providing thoughtful, creative, asset-based capital to companies in need is a passion for Scott. For the last 25 years, he has enjoyed building relationships and structuring deals in the Southwest region. During his time with FINOVA/TEXTRON, First Capital, and AloStar Scott utilized his consultative approach to capital solutions to become a trusted advisor for borrowers and referral sources, including junior and senior lenders and equity sponsors. Scott enjoys spending time with his wife, two daughters and son, chasing high school and extracurricular activities, as well as, Oklahoma State Cowboy sporting events.