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Stephen Mainello has a diverse range of work experience spanning over three decades. Stephen began their career in 1986 as a Project Engineer at The Whiting-Turner Contracting Company. Stephen then moved on to become a Senior Project Manager at Structural Preservation Systems in 1992. In 1995, they joined St. Paul Travelers as a Senior Claims Engineer and Surety Underwriter. Stephen's next role was at Allied North America, where they served as the Executive Vice President of Washington DC from 2004 to 2008. Currently, they are the Senior Vice President at RCM&D, a position they have held since August 2008.

Stephen Mainello obtained their Bachelor of Science degree in Civil Engineering from Penn State University, which they pursued from 1982 to 1986. Later on, from 1994 to 1996, they attended Loyola University Maryland, where they completed their Master of Business Administration (MBA) with a specialization in Finance.