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Joseph DiPesa has a diverse work experience spanning multiple industries. Joseph is currently working at Senior Life Insurance Company as Sales and Agent Support, where they help agents make sales and achieve their career goals through communication and organization. Joseph also plays a similar role at Temperate Legacy Group, an agency within Senior Life Insurance Company, focusing on expanding the group.

Prior to their current roles, Joseph was the President of DiPesa Insurance Group, starting in 2005. In 2012, they worked at NFP Thorbahn in Business Development. From 2020 to 2022, Joseph was at EverQuote, where they played a crucial part in the company's expansion, hiring and recruiting process, and creating commission structures for over 150 sales agents.

Joseph also has experience in the education sector, as they were the Owner of Millis Country Day School from 1997 to 2010. Joseph was a staff member at DiPesa & Co. from 1998 to 2004. Furthermore, they worked as the General Manager at F.J. O'Hara and Sons from 1986 to 1997.

Overall, Joseph DiPesa's work experience showcases their expertise in sales, agent support, business development, and leadership roles within the insurance industry, as well as their involvement in the education and hospitality sectors.

Joseph DiPesa attended Boston College High School from 1975 to 1979. After completing high school, they went on to enroll at Ithaca College from 1980 to 1984. At Ithaca College, they earned a Bachelor of Science degree in Business with a focus on Accounting.