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Rick Flagg has a diverse work experience spanning over several years. Rick started their career as a VP Administration at Noble Lowndes/Cowan Actuarial Co., where they managed data processing services and defined contribution plan administration. Rick then joined Marketware Computer Systems, Inc as a Groupware Practice Leader, where they founded and developed the Lotus Notes practice. After that, they worked at Collaborative Solutions, Inc. as the Founder and President, where they built the company from inception to a $500,000 per year business with five employees. Rick then joined Aurora Casket Company as the Director of Marketing, responsible for setting strategy and monitoring the execution of marketing messages and new product development. Following that, they worked at Chrysler as a Sr. Business Analyst, providing Lotus Notes analysis, development, and project leadership within the Shared Services team. Lastly, they joined OnTrak Software as a Product Manager and Chief Technical Officer, responsible for product development and management.

Rick Flagg attended the University of Cincinnati from 1975 to 1980, where they earned a Bachelor of Science degree in Business Administration with a focus on Marketing.