Bill Chesley

Consultant at Self

Bill Chesley is a seasoned operating company executive and strategic thinker with over 25 years of institutional and entrepreneurial management experience and a successful track record of leading organizations and repositioning companies for profitable growth. His success has demonstrated his ability to build, manage and motivate teams, form alliances and develop strategies with strategic partners, and design/implement enabling technologies. Through Bill’s leadership, strategic planning and innovative problem-solving, he has lead several organizations to achieving financial gains along with experiencing increased operational efficiency.

Bill was a co-founder and EVP of Finance and Operations of Breckenridge Insurance Services, a specialty property and casualty insurance
distribution company. Additional roles include CEO of Health Management Online, the first healthcare technology company to successfully automate a digital workers’ compensation bill submission process, COO of Pyramid Technologies, A leading provider of mission critical claims solutions for insurance professionals, and COO of AON Risk Resources, a holding company composed of Wholesalers, Facultative Reinsurance Brokers, technology businesses.


Expertises: B2B Sales, IT / Infrastructure, Lean Methodology
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