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Bob McKenna has over 20 years of work experience in the insurance industry. Bob began their career at Founders Insurance Company in 1984 and was promoted to Claims Vice President before being promoted again to Executive Vice President. During their time at Founders, Bob played a crucial role in the company's growth, helping it increase its surplus from $2.7 million to $30 million and its assets from $19 million to $90 million. Bob also helped improve the company's ratings from C-Best to A-Best.

In 2000, Bob joined America Worldwide Insurance Brokers as an Agency Manager, where they managed a start-up surplus lines agency, offering a variety of commercial and personal lines products.

In 2001, Bob briefly worked at American Service Insurance as a Litigation Manager before joining Atlas Financial Holdings, Inc. as a Litigation Manager as well. At Atlas, Bob focused on increasing profitability by recognizing realistic claim values and implementing legal flat fee arrangements. Bob also emphasized early recognition of claim injury severity through the use of software and reporting formats. Bob handled large exposure cases, corporate litigation, and attended claim mediations throughout the United States.

Bob McKenna attended Upper Iowa University, where they obtained a Bachelor of Arts (B.A.) degree. Their field of study was American History (United States), and they also pursued minors in Business and Psychology. The specific start and end years of their education at Upper Iowa University are not provided in the information given. Additionally, it is mentioned that Bob McKenna majored in History and Business and had a minor in Psychology at Upper Iowa University, located in Fayette, Iowa. No other details or experiences about their education history are provided.