Andrew Olson

Chief Strategy Officer at Enter


Andrew Olson is the current Chief Strategy Officer at Enter. Prior to this, they were with Enter, Inc. for 3 years and 6 months, where they held positions as the Chief Strategy Officer (CSO), Vice President of Finance, and Social Innovation Specialist. During their time as the Social Innovation Specialist at Enter, Inc., Andrew was responsible for leading organizational changes including enterprise restructuring, business unit transformation, and the implementation of data-driven operations culture and system. This included a data-science driven client-facing operations and reporting hub. Andrew also led the development of financial reporting policies and systems, as well as the diligence and securing terms for a USD 100 million credit facility, extensible to USD 300 million in six months. The analysis ultimately led to a major strategic shift for the organization and kicking off a major restructuring effort. In their role as the Social Innovation Specialist at GHHI, Andrew was responsible for Alternate Payment Models and Data science. Andrew created and managed contracting negotiations for adopting value-based purchasing arrangements addressing the social determinants for multiple state, plan, and provider relationships. Andrew also designed and coded data analysis software to identify high-risk populations from their claims, encounter, enrollment, and other external data; then calculate their baseline, historical, and forward-looking expected total costs as a basis for economic and financial analysis. Andrew has also authored over 10 publications on insurance market-dynamics and healthcare policy.

Andrew Olson has a Master of Arts from American University's School of International Service, a MBA from American University's Kogod School of Business, and a BA from Siena College. Andrew also has a Graduate Certificate from American University in International Politics and a Certificate in Foreign Policy from American University. Additionally, they have a BESS from Bloomberg Essentials.



  • Chief Strategy Officer

    Current role

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