Michelle Orlando Headshot

Michelle Orlando



Michelle graduated with honors from the University of Massachusetts at Amherst in 1982 with a degree in Business Finance and Law. During her undergraduate studies she interned for the Banking Commissioner’s office in Boston and the Office of Community and Economic Development in Pittsfield, MA.  

Michelle started her career at the Dunlap Corporation in 1983. She worked thirty years for them and their successor organizations Hilb, Rogal and Hobbs and Willis of Northern New England, most recently as their Senior Vice President of Bond Operations. Michelle is currently President of Cross Surety, Inc.  

Michelle has spent her entire career working with sureties, construction companies, public owners, corporations, and banks. She has gained the respect of the industry on a local and national level. Her advice has been sought after by many and she has been a featured speaker at many industry related events. She has also taught courses on several bonding topics.

Michelle is Vice President of the New England Surety Association, served on the National AGC Contractor’s Surety Bonding Committee, is a member and past director of the AGC of Maine, the Associated Builders and Contractors, Construction Financial Management Association, Maine Better Transportation Association and the National Association of Surety Bond Producers. Michelle is a recipient of the Tiger Trust Award from the National Association of Surety Bond Producers for excellence in the promotion of surety bonds. She has also been recognized for her volunteer efforts by the Big Brothers and Sisters of Androscoggin County Maine and the Girl Scouts.

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