In November 2003, John Sweeney demonstrated entrepreneurial spirit by acquiring Ray Sweeney Insurance Agency, a venture he embarked on after a decade of collaborative work with his parents. Initially, John, alongside his cousin Michael McCarthy, laid the foundation, and over the past two decades, John R. Sweeney Insurance has flourished through a combination of exceptional employees, organic growth, and strategic agency acquisitions.

John's commitment extends beyond the business realm, as evidenced by his decade-long service on the Town Council (2005-2015), culminating in his role as President during his final term. His leadership prowess further shines through his former Chair position at the Massachusetts Association of Insurance Agents, where he ascended from the Board to the Executive Board, holding various positions from 2011 to 2022. Currently, he serves as the President of the Hampden County Association of Insurance Agents.

A dedicated West Springfield resident, John, along with his wife Kimberly, takes pride in nurturing the academic journeys of their children, Madelyn and Patrick. Beyond professional and civic engagements, John generously contributes to the community, leveraging the business to sponsor various local organizations and events, including golf tournaments, school initiatives, sports teams, and charitable walks. John's enduring commitment to community well-being and leadership roles exemplify his profound impact on West Springfield.