Jameson Chiariello joined Bearingstar in March 2026 as a Personal Lines Specialist, focused on helping clients find the right coverage at the right value. Working in inside sales, he brings over a decade of experience in both insurance and banking, giving him a well-rounded perspective when it comes to protecting what matters most.
Jameson is known for being the person who can find a better deal, and he genuinely enjoys it. Whether he is reviewing coverage options or helping someone save money, he takes pride in being the one who comes through for clients.
Before joining Bearingstar, Jameson spent 12 years in the insurance industry and also worked in banking with Middlesex Savings Bank and Needham Bank. These roles helped him build a strong understanding of how people manage their finances and how thoughtful guidance can make a difference.
He earned his degree in Operations Management from UMass Dartmouth, which has supported his ability to think strategically and contribute as a team player throughout his career.
Originally from Millis, Massachusetts, Jameson now lives in Berkley with his family. Outside of work, he enjoys spending time with them, playing blackjack, and planning trips, often putting his deal-finding skills to good use.
At Bearingstar, Jameson brings a helpful, team-first mindset and a genuine commitment to making insurance easier and more accessible for the people he works with.
