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American Family Insurance CIO executive Sheldon Cuffie leaving company


Sheldon Cuffie
Sheldon Cuffie, American Family Insurance
Kenny Yoo/MBJ

An American Family Insurance executive based in Milwaukee is on the move.

Sheldon Cuffie, who has served in the chief information officer and chief information security officer roles at Madison-based American Family Insurance for the last four years, announced in a LinkedIn post that he is stepping down from the property and casualty insurer and taking time off before his "next great adventure."

"For now, l'll be doing a bit of advisory work, continuing external board assignments, and supporting our community efforts to make Milwaukee a better place to live, work, and play," Cuffie wrote in the post.

"I'm most grateful for the opportunity to help others realize their dreams," the post continued. "Over the past four years, we've delivered on internal re-skilling outcomes, developed and promoted talent into leadership roles, engaged in tech apprenticeship programs, and created partnerships to train underemployed talent in Southeastern Wisconsin in cloud computing. Some of this talent now works for AmFam, but the whole region benefits as there is more talent available to support an ecosystem of technology and growth."

Cuffie started with American Family Insurance in December of 2019 as its vice president and enterprise chief information security officer. His job was to consolidate the cybersecurity programs across the group's five companies, which are American Family Insurance, CONNECT, The General, Homesite and Main Street America Insurance.

After completing that task in less than 18 months, he began overseeing the company's technology infrastructure, cloud computing and digital workplace tools. He was promoted again in late 2022, becoming the company's enterprise chief information officer. He now also oversees functions that support "the business of IT," as he described it, including information technology (IT) finance and IT vendor management.

Prior to American Family Insurance, Cuffie had an executive role with Dell Technologies in Austin, Texas.


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