Rob DiMase


CRO, Partner

Professional Experience

As Sentinel’s Chief Revenue Officer (CRO), Rob oversees all revenue-related functions, including sales, marketing and client support. He manages pricing strategies and ensures Sentinel's benefit plans are competitively priced and effectively communicated to clients.

Rob has held many other positions at Sentinel over the years, including Director of Finance and Head of Sales. His expertise in benefit plan design and administration allows the company to provide its clients with high-quality, cost-effective plans tailored to their unique needs.

Rob's years of experience have given him a deep understanding of employee benefits and the skills needed to lead the company's revenue-related functions. As President of Sentinel Insurance Agency and CRO, he plays a critical role in the company's success and growth.

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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