A senior practitioner with independent agencies, brokerages and insurance consulting firms, Mr. Cunningham began his career with Cunningham Insurance Group,a suburban Chicago brokerage specializing in professional liability and middlemarket commercial accounts. At that firm, he was senior vice president and chief operating officer. In addition to his management responsibilities, he also worked as a producer and thereby developed extensive experience in all areas of the insurance distribution system, from sales and marketing to finance, IT & systems, and agency-company relationships.
In 1987, he accepted a position as principal with Hales & Associates a Chicago-based insurance financial consulting and investment banking firm. Mr. Cunningham specialized in merger and acquisitions and valuations. He also edited the Hales Report, a monthly newsletter containing coverage and analysis of the insurance industry with a focus on the distribution sector.
In 1997, Mr. Cunningham joined IMCG, a Kansas City-based business management consultancy specializing in start-ups and mergers. As a principal, he worked exclusively with insurance clients. Wishing to extend his consulting services beyond individual transactions, Mr. Cunningham formed OPTIS Partners, LLC, in 2002.
Interviewed and quoted extensively in the business press and industry publications, Mr. Cunningham is the past president of the Chicago Board of Underwriters. He has held adjunct faculty positions at Triton College and Morton College, as well as leadership positions with a number of insurance organizations, including the Harold H. Hines Memorial Symposium Committee. Mr. Cunningham holds a BA in business management from Lewis College, with a focus in finance and accounting.