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Cliff Lee began their work experience in 1991 as a Senior Manager at Accenture, where they focused on healthcare, artificial intelligence, and financial services projects. Cliff then worked at Marketsoft as the Director of Professional Services before the company was acquired by Unica and later IBM. In 2003, they founded and served as the CEO of Redtree Consulting, providing business, strategy, and technology consulting services to clients such as Veritas, Microsoft, and Wells Fargo. From 2013 to 2016, Cliff was the Vice President of Healthcare Products & Solutions at Mobiquity Inc., a mobile and digital consulting company, where they developed various digital health products, including regulated solutions for remote patient monitoring and engagement. Cliff then served as the Managing Director of a digital health startup called Nusa Health, where they designed and launched a digital health solution for Singapore and Yogyakarta, Indonesia. In 2017, they joined BrightInsight as the Head of Product and later became the Vice President of Product Management, overseeing the development and launch of a regulated platform product. Most recently, in 2023, Cliff joined Dawn Health as the VP of Digital Health Strategy.

Cliff Lee possesses a Master of Business Administration (MBA) with a focus on Global Management from the Babson F.W. Olin Graduate School of Business. Prior to this, they received a Bachelor's degree in Industrial Engineering and Operations Research from the University of Massachusetts Amherst. In addition to their formal education, Lee has obtained several certifications. In 2013, they completed the Salesforce.com Platform Configuration and Administration certification from OpFocus, Inc. Additionally, Lee has attained various certifications in the field of Artificial Intelligence (AI) and Machine Learning. In 2017, they obtained certifications in Machine Learning and Google Cloud Platform from Coursera. More recently, in 2021, Lee completed certifications in Becoming an AI-First Product Leader and Improving Your Listening Skills, both offered by LinkedIn.