Building Trust at Scale: Dr. Toyin Ajayi of Cityblock Health on Fixing Incentives in Healthcare

Dr. Toyin Ajayi, co-founder and CEO of Cityblock Health, joins the Five Mile Difference to share how she built one of the most mission-driven and financially rigorous companies in digital health, serving Medicaid members and dually eligible patients who the rest of the healthcare system has largely ignored. In this conversation, Joe and Dr. Ajayi discuss: Why value-based care for Medicaid is one of the biggest opportunities in healthcare The early insight that trust, not just technology, drives better outcomes How Cityblock measures trust with a validated member tool What their first major contract taught them about engaging hard-to-reach populations How AI is enabling true personalization at scale for low-income communities What it takes to become an AI-native organization when you didn't start that way