John Flaherty

Executive Vice President
John Flaherty, Image

John has been with Berkshire Insurance Group (BIG) since September 2019. John is a dynamic, passionate, producing leader that looks to engage/unite employees and customers within their four insurance divisions of Commercial, Personal, Employee Benefits and Individual products. John has been an Independent Contractor since 2017 with OneDigital, who purchased and partners with BIG’s Employee Benefits division since 10.01.2020.

John’s over 30 years of insurance experience includes growing insurance practices via team building, sales, mentoring and high-level consulting. His financial sharpness and business creativity, while giving to his internal and external network honestly and authentically has kept him motivated for over three decades. John was a partner at Longfellow Benefits in Boston, where he worked for 18 years and helped grow and lead their employee benefit practice; Longfellow sold to Gallagher in December 2013.

John graduated from Norwich University – The Military College of Vermont in 1986 and received his Master in Business Administration (MBA) in 1989 from Northeastern University, where he taught Accounting and various business classes for over 27 years.