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Matthew Skidmore has extensive work experience, starting from their role as an Operations Manager (Platoon Leader) in the US Army from 2006 to 2007, where they managed mission planning and execution for helicopters supporting various operations. Matthew then served as an Assistant Manager (Executive Officer) and Assistant Operations Officer in the US Army from 2007 to 2009. From 2010 to 2012, they worked as an Engagement Manager (CIED Task Force Commander) and Senior Operations Manager (Company Commander) in the United States Army, where they provided strategic consulting services and project leadership related to Improvised Explosive Devices. Additionally, they received a Bronze Star for their services. Matthew Skidmore subsequently held roles as a Product Manager at Seattle Aero from 2012 to 2014, a Consultant at West Monroe Partners from 2014 to 2016, and a Senior Solutions Consultant at Infor from 2016 to 2018. Matthew then worked as a Senior Solutions Engineer at Oracle from 2018 to 2021. Currently, Matthew Skidmore is the NA Team Lead/Solution Engineering at SugarCRM, leading a complex team of Solutions Engineers.

Matthew Skidmore's education history includes various military and civilian certifications. Matthew completed the Leadership Development program, with a focus on the Captains Career Course, at the United States Army Aviation Center of Excellence in 2009-2010. In 2006, they obtained the Ranger Qualified designation from the United States Army Ranger School, specializing in Military and Strategic Leadership. From 2004 to 2006, they studied at the United States Army Aviation Center of Excellence, earning a degree as a US Army Aviator, specializing in UH-60 Blackhawk Helicopter operations. Prior to that, they attended Cedarville University from 1999 to 2004, where they earned a Bachelor of Arts degree in Sport Management and Business. In addition to their academic achievements, Matthew Skidmore also holds certifications such as Microsoft Certified Professional (MCPS) and Microsoft Dynamics Customization and Configuration in CRM 2013 (MS), obtained in 2015, as well as a Commercial Pilot (CP) certification from the Federal Aviation Administration, obtained in 2006.