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Craig Bassingthwaite has a diverse work experience spanning over two decades. Craig started their career as a Supply & Logistics Specialist in the US Army from 1995 to 1998. Following this, they worked at Peerless Insurance as a Sr. Field Adjuster from 1999 to 2003, handling auto and property claims. Craig then joined OneBeacon Insurance Group as a Claims Supervisor, where they managed staff, vendors, and conducted audits. From 2006 to 2008, Craig worked at MiddleOak as the Vice President of Property Claims, overseeing activities and personnel in the department. Craig then moved on to Acadia Insurance, where they held the position of Property Claims Manager and Catastrophe Manager, responsible for the overall department's functioning and strategic planning. Currently, Craig is employed at Varney Agency as the Senior Vice President, managing claim and risk management activities across multiple agency locations and insurance companies, with a specialization in complex, high-value claims.

Craig Bassingthwaite attended Monadnock Regional High School from 1989 to 1992. After completing high school, they enrolled at the University of New Hampshire in 1992 for a year, where they studied marine biology. In 1993, they transferred to Keene State College, where they focused on health and fitness management for two years. Craig then pursued a Bachelor of Science degree in public management with a minor in health and fitness management from Austin Peay State University from 1996 to 1998.