The Five Mile Difference, Episode 3: Driving Innovation in Healthcare

Episode 3: Driving Innovation in Healthcare

The importance of behavioral economics, rapid experimentation, and the role of policy in driving healthcare innovation.

Guest: Roy Rosin, Board Partner, First Round Capital & former Chief Innovation Officer, Penn Medicine

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Episode Description:

In this episode of The Five Mile Difference, host Joe Kitonga sits down with Roy Rosin, Board Partner at First Round Capital and former VP of Innovation at Intuit and Chief Innovation Officer at Penn Medicine, for a compelling conversation on what it really takes to move the needle in healthcare.

They explore the "Five Mile Difference" in life expectancy in Philadelphia and unpack Roy’s journey from leading innovation in tech to transforming healthcare delivery at Penn Medicine. Roy shares lessons learned, common pitfalls in healthcare innovation, and where he sees the most promise, especially as AI, behavioral economics, and telehealth continue to evolve.

This episode dives deep into the structural, behavioral, and systemic levers that can drive meaningful change, with an emphasis on collaboration, empathy, and persistence.

We cover:

• Why healthcare innovation requires a mission-driven mindset
• How behavioral economics can improve outcomes
• The rising potential of disruptive innovation powered by AI
• How telehealth is evolving beyond just digitizing care
• The importance of cross-sector collaboration
• How regulation can unlock new opportunities
• Addressing social determinants of health for equity
• The role of rapid experimentation in finding what works
• Why empathy and storytelling matter in stakeholder engagement
• The need for relentless persistence in this complex industry

About our guest:

Roy Rosin is a seasoned innovation leader with a track record of building and scaling impactful programs. He spends most of his time at First Round in the healthcare space, drawing from his experience as Chief Innovation Officer at Penn Medicine. During his 12-year tenure, his team designed, tested, and implemented 150 technology-enabled interventions across care delivery.

These novel solutions decreased readmission rates, ER utilization, morbidity, hospital stays, and clinician burden while increasing adherence, screening, patient engagement, quality of life, and use of high-value sites of care. Earlier in his career, Roy built and led the innovation program at Intuit, where he spent 18 years. Starting as the product manager of Quicken, he helped grow it into the top-selling consumer software application with 14 million consumers. After five years of redesigning entrepreneurial practices, which were also applied to existing businesses,

Intuit delivered shareholder returns 33x the S&P 500. Throughout his career, Roy has learned from some of the best, including Scott Cook, Bill Campbell, and Brad Smith at Intuit, as well as leading behavioral scientists at Penn, and remarkable founders who showed him how hard things could become possible. He received his MBA from Stanford and graduated with honors from Harvard College as a John Harvard Scholar.

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