Rob DiMase


CRO, Partner

Professional Experience

Serving as CRO and President of Sentinel Insurance Agency, Rob has been a driving force behind Sentinel's growth since he started as one of the company's first employees. With years of experience and a profound understanding of employee benefits, he possesses a unique insight into sales strategy.

Rob’s expertise in benefit plan design and administration enables Sentinel to provide its clients with high-quality, cost-effective plans tailored to their unique needs. As the leader of all revenue-related functions, Rob ensures that Sentinel's benefit plans are competitively priced and effectively communicated to clients.

Outside of the office, Rob serves on multiple advisory boards, including Labouré College of Healthcare, Blue Cross Blue Shield of MA, Harvard Pilgrim large group broker advisory boards, and the NABIP board of directors. He regularly participates in SentinelCares initiatives, finding particular enjoyment in those involving outdoor activities.

Fun fact about Rob: Growing up, he was a ball boy at tennis tournaments and has worked many airshows around the country.

Educational Background and Certifications

  • Boston College, Chestnut Hill, MA – Bachelor of Science – Finance
  • The Commonwealth of Massachusetts – Life, Accident and Health Insurance agent and advisor
  • Accredited Investment Fiduciary®, AIF®
  • FINRA Series 6, 63 & 65
  • PPACA Certified


Needham, MA

Out of the Office

Rob enjoys skiing, tennis and spending time with his family in Vermont.

Personal Quote

“When I originally entered the employee benefits field, my intent was to work with companies to determine what career path I eventually wanted to take. With over 25 years in employee benefits I haven’t found anything I enjoy better!”

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