David L. Middlemiss is a distinguished entrepreneur and financial expert, renowned as the Founder and CEO of Prodigy Benefit Management. Graduating from Syracuse University in 1991, David laid the groundwork for his illustrious career in finance.

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Beginning his journey within his family's company, David garnered invaluable experience in business operations and management. In 2001, he ventured into the realm of financial services, joining New York Life as a Financial Representative. His expertise flourished as he later assumed roles as a Financial Advisor with Lincoln Financial Advisors and Mass Mutual, showcasing his proficiency in wealth management and strategic financial planning.

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In 2012, David's exceptional skills were acknowledged by Syracuse University, where he was honored as a Preferred Advisor for alumni estate and gift planning—a testament to his expertise and dedication to serving his community.

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In 2014, David embarked on his entrepreneurial venture by founding HW Syzygy, marking the beginning of his foray into benefit management solutions. His visionary leadership and commitment to excellence propelled HW Syzygy to success, culminating in its merger with Pentum Group in 2019, forming Prodigy Benefit Management.

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As the driving force behind Prodigy Benefit Management, David continues to lead with innovation, leveraging his extensive industry experience to provide tailored benefit strategies for individuals and businesses. His unwavering commitment to client satisfaction and relentless pursuit of excellence solidify his status as a trailblazer in the financial services sector.

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David L. Middlemiss is not only a distinguished entrepreneur and financial expert but also a devoted family man and community advocate. Married to his wife of 21 years and father to their daughter Kate, David embodies the values of commitment and compassion both in his personal and professional endeavors.

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In addition to his accomplishments in finance, David has also pursued his passion for soccer. He earned his Class D coaching license from US Soccer and is recognized as a goalkeeping specialist, demonstrating his dedication to the sport and nurturing talent on the field.

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Beyond his professional and sporting achievements, David and his family, including their beloved dog Tupper, are actively involved in fostering dogs for adoption through Second Chance Rescue of Central NY. Their commitment to animal welfare underscores their altruism and sense of community responsibility.

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David Middlemiss's multifaceted life reflects his unwavering dedication to excellence, whether in business, sports, or community service. His leadership, compassion, and commitment to making a positive impact continue to inspire those around him.