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Tobin Winters has a diverse work experience in various roles and industries. Tobin is currently serving as the Director of Engineering at Vermont Mutual Insurance Group since June 2020. Prior to this, they worked as the Vice President of Engineering at Mi9 Retail from November 2018 to March 2020. Tobin also held several roles at MyWebGrocer, including Director of IT Operations, Software Development Manager, and Software Engineer, from June 2014 to November 2018. Before that, they worked at Computac, Inc. as an Application Architect from May 2013 to June 2014. Tobin spent a significant portion of their career at Computac, Inc. as a Product Manager and Application Developer from July 2003 to April 2013. Tobin also worked as an Adjunct Professor at Franklin Pierce University, specializing in I.S. courses, from May 2009 to June 2012.

Tobin Winters earned a Bachelor of Science degree in Information Technology - Systems Analysis and Design from Granite State College in the years 1999 to 2003. Afterward, from 2005 to 2009, they pursued a Master of Science degree in Information Technology Management from Franklin Pierce University. In May 2020, Tobin also received the certification of Google Cloud Certified Professional Cloud Architect from Google.