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Ben Cawley has a diverse work experience. Ben began their career in 1996 as a Lab Assistant at Dekalb Genetics Corporation, where they worked until 1998. In 1998, they joined Guide Dogs for the Blind as a Guide Dog Mobility Instructor and stayed with the company until 2012. Additionally, from 2004 to 2011, Ben worked as a Dog Training Consultant for Paws and Claws Pet Service, where they utilized their expertise to assist clients in improving their relationship with their dogs. In 2012, Ben joined Guiding Eyes for the Blind. Ben initially held the roles of Class Supervisor and Director of Admissions before transitioning to their current position as Director of Client Experience.

Ben Cawley attended Windham High School from 1988 to 1992. Ben did not pursue any specific degree or field of study during this time. Following their high school education, Ben went on to study at Fairfield University from 1992 to 1996. Ben obtained a Bachelor of Science degree in Biology during their time at Fairfield University.