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Jon Crosby has a diverse work experience spanning several roles and companies. Jon started their career as an IT Helpdesk Manager at The Sleep Train, Inc, where they managed a team responsible for providing technical support. Jon then worked as a Quality Assurance Manager, leading loss prevention functions and software quality management. Later, Jon became the Director of Information Technology at The Sleep Train, overseeing IT operations and strategic planning. Jon also served as the Director of IT App Development at Mattress Firm, managing development teams and supporting enterprise platforms.

Jon's experience also includes roles at Telecom Infra Project and Meta, where they served as a TIP DevOps Team Leader and IT Operations and App Development Team Leader, respectively. At Launch Consulting Group, they held various positions, including Director of Client Solutions and Senior Project Manager, where they helped businesses with technology and innovation initiatives.

Currently, Jon operates their own consulting company, Jon Crosby Consulting, providing technology consulting services to small and medium-sized businesses. Additionally, they have recently started working as the Director of Technology & Integrations at Tamazari.

Jon Crosby attended California State University-Sacramento from 1994 to 2002, where they obtained a Bachelor's Degree in Mechanical Engineering.