Title: President and Chief Executive Officer
Company: Cherrywood Enterprises LLC
Location: Orlando, Florida, United States
Craig M. Geisler, president and chief executive officer at Cherrywood Enterprises LLC, has been recognized by Marquis Who’s Who Top Business Owners for dedication, achievements, and leadership in finance.
With nearly a decade and a half of experience, Mr. Geisler has established a successful career in finance, specializing in the acquisition, underwriting, review, and optimal resolution of charged-off portfolios from banks, credit unions, auto lenders, and commercial lenders. He currently serves as the president and chief executive officer of Cherrywood Enterprises LLC, a position he has held since 2012. In this role, he leads a team that markets to industry owners, including banks, credit unions, auto lenders, and commercial lenders. His responsibilities include setting up calls to discuss charged-off portfolios, overseeing underwriting processes, managing pricing expectations, presenting offers to lenders, and finalizing purchases. His previous experience includes serving as vice president at Wellington Acquisition Group LLC from 2012 to 2015, chief operating officer at Mattia and Associates from 2009 to 2012, account manager at Creditmax from 2007 to 2009, loan officer at Palm Beach Mortgage Group from 2005 to 2007, loan officer at HomeBanc Mortgage from 2003 to 2005, and director of investor relations at NewsMax Media Inc. from 1999 to 2003.
Mr. Geisler is an active member of several professional organizations, including the American Collectors Association Inc., the Arkansas Bankers Association, the Michigan Bankers Association, the Oregon Bankers Association, the Tennessee Bankers Association, the Utah Bankers Association, the Colorado Bankers Association, and the Iowa Bankers Association. His achievements include being voted “One of the Most Iconic Businesses to Watch Out For” in 2024, being interviewed for Entrepreneur Magazine, and receiving the “World’s Greatest Dad” award from his daughter. He also donates his time to charitable causes such as St. Jude Children’s Research Hospital and Feed My Starving Children.
Reflecting on his journey, Mr. Geisler recalls the significant downturn in the real estate market in 2009. During this time, he actively sought new opportunities and was approached by Credit Max after they discovered his resume online. Initially hesitant about the role due to his reservations about collections work, his perspective shifted when he learned that Credit Max focused on debt purchasing rather than collections. Intrigued by this concept, he attended an interview and was immediately drawn to the company’s vision. The training he received at Credit Max proved invaluable during his three-and-a-half-year tenure with the company. His subsequent experiences with other debt-buying entities further deepened his understanding of the industry and highlighted areas for improvement. In 2012, he co-founded Cherrywood Enterprises with his brother. The company was built on the principles of prioritizing client needs, maintaining professionalism, and addressing the shortcomings of previous entities to establish a stronger and more effective business model.
Mr. Geisler takes great pride in his family, who have played an instrumental role in shaping him into the person he is today and attributes his success to their unwavering support. Additionally, he has been fortunate to be mentored by some of the most influential figures in the industry, whose guidance has been crucial to his rise to the top. One of the most significant lessons he carries with him is the work ethic instilled by his father from a young age. As he ventured into business, his father reminded him that they share the same last name, emphasizing the importance of treating people with respect and integrity. In the coming years, he is determined to continue pursuing his passion for the industry while making a significant impact on society by helping those in need. He is especially committed to being a source of pride for his family and wife, striving for success that resonates with them. He is also dedicated to supporting military veterans, having witnessed the struggles many face with homelessness, by making a meaningful difference in their lives and ensuring they receive the support and recognition they deserve.
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