Troy Caraway

Troy Caraway brings more than 30 years of executive leadership experience across healthcare technology, services, and payer markets, with a track record of leading large-scale businesses, accelerating growth, and driving strategic transformation.

At Machinify, Troy leads commercial strategy and operations, including Growth, Marketing, Client Success, and Implementations. Prior to joining Machinify, Troy served as President of Post-Acute Care and subsequently President of Emerging Markets at WellSky, where he held significant P&L responsibility, helped establish the company's payer business, and contributed to its growth and strategic expansion.

Previously, Troy held senior executive roles at UnityPoint Health, including serving as CEO of Physicians Plus Insurance Corporation. There, he led risk-bearing businesses, developed payer strategy, and spearheaded the formation of a new multistate health insurance company through a strategic partnership.

Earlier in his career, Troy held senior leadership positions at Optum, spanning enterprise growth, strategic accounts, and business development.

Troy holds a Bachelor of Science degree from California Polytechnic State University, San Luis Obispo.