Overview
Dennis Hillen serves as National President at Pearl Health [1][3]. Hillen is a cross-functional leader with expertise across technology, finance, strategy, and digital health product development, with experience ranging from startups to Fortune 100 organizations [2]. Hillen's career includes roles at Oscar Health as SVP - National Market P&L Leader / Insurance Strategy from 2021 to 2025 and VP - Southeast Region Market P&L Leader from 2020 to 2021 [4][5]. Prior to Oscar Health, Hillen held multiple positions at Humana spanning from 2008 to 2020, including roles in financial reporting, innovation and marketing finance, strategic finance, product development, and enterprise transformation [6][7][8][9][10]. Hillen holds an MBA from Indiana University Southeast and a BBA in Finance from the University of Kentucky [11][12].
Profile introduction
Cross-functional leader consistently tasked with strategy/business model development, horizontal/matrixed team alignment, and tactical execution of transformational board-level initiatives. Brings a broad expertise across technology, finance, strategy, and digital health product development honed over varied experiences ranging from startups to Fortune 100 organizations. Strong track record of significant results made possible by fostering collaboration within matrixed, cross-disciplinary teams to quickly define and execute ambitious initiatives.
Career history
- National President2025 to presentPearl Health
- SVP - National Market P&L Leader / Insurance Strategy2021 to 2025Oscar Health
- VP - Southeast Region Market P&L Leader2020 to 2021Oscar Health
- AVP - Enterprise Transformation2019 to 2020Humana
- Director of Product Development - Head of Innovation Strategy - Provider Platform / Solution Owner2014 to 2019Humana
- Director of Finance - Strategic Finance / Corporate Services CFO2012 to 2014Humana
- Finance Manager - Innovation and Marketing2010 to 2012Humana
- Finance Consultant - Financial Reporting2008 to 2010Humana
Education
BBA, FinanceUniversity of Kentucky
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