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Jesse Dickert has a wide range of work experience across various industries and roles. In 2008, they worked as a Sales Operations - IT Specialist at Orion Energy Systems, Inc., where they handled technical administration and development tasks for Microsoft Dynamics CRM and SharePoint Server. From 2011 to 2013, they served as a CRM Application Consultant at Ledgeview Partners, participating in all aspects of CRM implementation for customers. In 2013, they became the Salesforce.com Manager at Berkshire Hathaway Travel Protection, overseeing the Salesforce development team and system architecture. In 2016, they joined Rehrig Pacific Company as an Enterprise Software Manager. From 2018 to 2019, they worked as the Director of Innovation and Growth at Elexa Consumer Products, Inc., collaborating with various departments to drive innovation and growth using internal platforms. In 2019, they co-founded Spotz, a platform that modernizes community rental experiences, and served as the Co-founder and CTO. Additionally, they owned FIRE Fitness Camp Waupaca from 2019 to 2023 and FIRE Fitness Camp Wega from 2020 to 2022. Currently, they hold the role of Vice President at CoX, working on the TruLight project. Overall, Jesse Dickert's experience spans entrepreneurship, leadership, innovation, and technology management.

Jesse Dickert completed their education in the field of Computer Science and Computer Information Systems. From 2001 to 2004, they attended Madison Area Technical College and obtained a degree in Computer Information Systems with a concentration in Programmer/Analyst. Afterward, from 2004 to 2007, they pursued further studies at the University of Wisconsin-Stevens Point in the field of Computer Science, but the degree obtained is not specified.

In addition to their formal education, Jesse Dickert has obtained several certifications. In April 2019, they obtained certifications in Inbound Marketing, Inbound Sales, Social Media, and Sales Software from HubSpot. They also possess a Microsoft Certified Technology Specialist certification in Microsoft Dynamics CRM 2011 Customization and Configuration, although the exact date of obtaining this certification is unknown.