Jon began his career with the Home Insurance Company in Providence, RI, in 1977 as a commercial Casualty Underwriter. He later transferred to North Haven, CT, where he specialized in Inland and Ocean Marine Insurance as well as fidelity and surety bond underwriting. He later worked for the Hartford Insurance Company of Manchester, NH, as Marine Manager traveling throughout New England.

In 1984, he purchased The Archie Slawsby Insurance Agency, Inc., from Mr. Slawsby’s estate and began a rebuilding and acquisition phase that continues to the present. He earned his Certified Insurance Counselor (CIC) designation in 1989 and his Certified Insurance Wholesaler (CIW) designation in 1996. He has served on numerous insurance industry committees and advisory boards, and is a member of the Independent Insurance Agents and Brokers of America, The National Association of Professional Surplus Lines Offices, The American Association of Managing General Agents, and the National Alliance for Insurance Education and Research. In July of 2018, Jon sold the business to Karen Edgerton.