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Rich O'Boyle has a diverse work experience spanning over two decades. Rich started their career as a Project Manager at Kinko's and then worked as a Service and Support Technician at Dataserv. Rich later became a Manager and IT Consultant at Lundeen's Liquor. In 2005, they joined OfficeMax, where they served as a Pricing Team Technology Specialist, Pricing Team Marketing and Sales Analyst, and Senior Analyst and Sales Engineer. In 2008, they joined Lexmark as a Professional Services Engineer, Business Development Manager, and Business Consultant. Currently, they are working at ACDI and has held various roles, including Solutions Architect, Professional Services Manager, Regional Solutions Manager, and currently, as the Regional Sales Director. Rich's work experience revolves around sales growth, partner success, developing sales strategies, and providing effective solutions to business challenges.

Rich O'Boyle attended Northern Illinois University from 2003 to 2005, where they studied Communication. Prior to that, from 1995 to 1998, they attended Kent State University and pursued a field of study in Management Information Systems.