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Michael W. Flanagan has held a variety of roles in the technology industry since 2000. Michael W. began their career as Director of Sales for Essential Logic, LLC in 2000. Michael W. then went on to become National Sales Manager for BuyerZone.com in 2002 and Sales Director for SellPoint, Inc. in 2008. In 2010, they were promoted to Director, National Sales for Searchandise Commerce, which was later acquired by RichRelevance. At RichRelevance, they held the roles of VP, Strategic Accounts, Sr. Director Sales, and Director, Retail Personalization Solutions / Eastern Division from 2011 to 2015. Michael W. then moved to True Fit Corporation, where they were Area Vice President, Sales from 2015 to 2017. In 2017, they joined Monotype as VP Sales, Monotype & Olapic. In 2019, they were promoted to Regional Vice President of Sales at Pepperjam, and in 2020 they became Sr. Director B2C Sales at PixelMEDIA. Most recently, in 2022, they joined RafterOne as VP, Advisory Solutions - B2C Commerce.

Michael W. Flanagan obtained a Bachelor of Science (BS) in Business, Management from Keene State College. Michael W. also holds certifications in Certified Facilitator - Command of the Message from Force Management, Conceptual Selling from Miller Heiman Group, and Strategic Selling from Miller Heiman Group.