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Cynthia Benjamin has a long and varied work experience. Cynthia began their career in 1985 as a Product Design Engineer at IDEO Product Development. In 1989, they founded and became President of Samson-McCann, Inc. In 1998, they joined Strategic Decisions Group as a Senior Engagement Manager, leading strategy and management consulting teams. In 2006, they joined IMS Health as a Director of Innovation, leading the creation of a Big Data and Health IT growth platform. Cynthia also served as an Innovation Lab Principal and Global Process Lead, as well as a Principal, Strategy and Portfolio Analytics Consulting. In 2014, they became the Director of Design and Innovation at Thrive Foundation, where they led the foundation's tool and resource development initiatives. In 2016, they began working as an independent consultant for Strategy + Innovation + Impact. In 2017, they became the CEO and Co-Founder of Together Senior Health, the leading digital therapeutic and community platform for people with Alzheimer’s or cognitive decline. Cynthia also teaches at Stanford University's d. school, providing design and forecasting frameworks to innovators.

Cynthia Benjamin has an education history that includes a MBA from the University of California, Berkeley, Haas School of Business in Management of Technology (1995-1997), a MS from Stanford University in Mechanical Engineering/Product Design (1986-1988), a BS from Stanford University in Product Design Engineering (1981-1985), and a Semester at Sea, Institute for Shipboard Education (no degree).