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Jeffrey Chesky

Jeffrey Chesky

Jeffrey Chesky is the founder, chairman and CEO of Insuritas, the nation’s leading insurance agency reengineering solution. Insuritas deploys large, private-labeled “meta insurance agencies” that connect customers to insurance products in a frictionless shopping experience, eliminating the industry’s legacy distribution and technology platforms.

Chesky was the founder and president of Banc Insurance Services, where he pioneered the design, installation and outsourced management of insurance agencies for financial institutions nationally, and developed the meta agency platform. BIS was purchased by Jack Henry & Associates, one of the nation’s leading credit union core processing firms in 2004. Chesky led an MBO to reacquire the company from Jack Henry in June 2008 and renamed it Insuritas. In 2012, Chesky successfully executed a series A growth capital raise of $10 million to further invest in the meta agency digital distribution platform.

Chesky has also pioneered the development of the nation’s leading management consulting practice for insurance agency integration and growth strategies for meta agencies called IAPPEX: the Insurance Aisle Peak Performance Exchange.

Chesky has more than 30 years’ experience in the banking and insurance fields. He has served as a senior vice president of one of the nation’s 100 largest insurance agencies, director of institutional investment management at Mass Mutual Insurance Company and vice president of mortgage lending at both Fleet Bank and Bank of New England. Chesky also had the honor to serve on the White House staffs of President Jimmy Carter and Vice President Walter Mondale.

Recent Articles by Jeffrey Chesky

What GoogleCompare Shows on LeadGen

Steve Jobs was famous for saying; “A lot of times, people don’t know what they want until you show it to them.” He was most often referring to focus groups and “industry experts” as the last places he’d look for ideas on innovation and disruption. I’ve often wondered what Jobs would have said if asked […]

Uber’s Thinking Can Reinvent the Agent

I read the article Nick Lamperelli wrote after attending the Insurance Disrupted conference titled “No, Insurance Will Not Be Disrupted,” with his conclusion that there are insurmountable barriers to the “Uberization” of insurance. I’ve developed great respect for Nick’s perspectives. But our team at Insuritas disagrees. We think disruption within insurance (at the Uber level) is […]

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