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Dennis DePaola began their work experience in 1995 at Gutman, Mintz, Baker & Sonnenfeldt, where they served as a Senior Associate until 1998. In 1998, they joined Orsid Realty Corp as the Executive Vice President and General Counsel, a role they continue to hold.

Dennis DePaola completed their Bachelor of Science degree in Business Administration, Management, and Philosophy from Le Moyne College in 1993. Following this, from 1993 to 1996, they pursued a Juris Doctor degree in Law at St. John's University, School of Law.