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

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.

Beyond prescriptions: A primary care-led path to long-term weight loss

GLP-1 medications, such as semaglutide and tirzepatide, have seen a surge in popularity for weight loss, but behind the hype lies a growing concern: are we trading safety for convenience? With more and more programs offering prescriptions without proper evaluation or follow-up, many patients are left navigating powerful medications on their own.

In this episode, we dig into what GLP-1s are, why they work, and what’s being missed in today’s one-size-fits-all approach. Host and Vitable CEO Joe Kitonga is joined by Dr. Kate Baron and Dr. Michael Ash Shaub of Vitable Health to talk about the risks of low-touch prescribing, the importance of primary care oversight, and how long-term success depends on more than just a shot.

We cover:

💉 How GLP-1s work and why they’re so effective for weight loss

⚠️ The dangers of unsupervised use—from thyroid risk to nutritional deficiencies

🧠 Why behavioral support and lifestyle changes matter just as much as medication

🏥 The role of primary care in creating safer, more sustainable outcomes

📉 What happens when patients stop GLP-1s without a plan—and how to avoid it

—

About our guests:

Dr. Kate Baron is Head of Medical at Vitable Health, where she oversees medical operations, ensures clinical excellence, and drives innovation in virtual care delivery. As a Board Certified Family Physician with experience scaling early-stage digital health companies, Dr. Baron’s work centers on expanding access to primary care, improving chronic disease management, and delivering patient-centered, high-quality care.

Dr. Michael “Ash” Shaub is the Chief Clinical Officer at Vitable Health, where he oversees clinical strategy and clinical operations. With a background in both medicine and business, he’s passionate about building world-class comprehensive care models that improve access, outcomes, efficiency, and the patient experience - especially for working adults often left behind by traditional healthcare.

What causes a 20-year life expectancy gap between two zip codes just five miles apart?

In the premiere episode of The Five Mile Difference, Joseph Kitonga, founder and CEO of Vitable Health, sits down with Tom Sondergeld, former VP of Global Benefits & Mobility at Walgreens Boots Alliance, the multinational company that owns Walgreens, to unpack one of healthcare’s most urgent challenges: closing the access gap for Americans.

Drawing on his experience leading benefits for a workforce of over 250,000 employees and managing $2B a year in healthcare budget, Tom shares what it takes to design equitable health plans, what employers get wrong about engagement, and why the U.S. must shift from a sick-care system to one focused on prevention. The conversation spans the evolution of digital health, behavior change, the role of GLP-1s, and innovations like ICHRAs and level funding.

About Tom Sondergeld

Tom Sondergeld is a nationally recognized leader in healthcare and employee benefits strategy with over 30 years of experience driving transformation across Fortune 50 companies, startups, and global organizations. As the former Vice President of Global Benefits at Walgreens Boots Alliance, he led healthcare programs for one of the largest workforces in the world, delivering innovative solutions that saved hundreds of millions of dollars without raising costs for employees.

Today, Sondergeld is the founder and Managing Partner of TS Consulting Services, where he advises startups, employer groups, transparent PBMs, and private equity-backed healthcare ventures. He also serves as a senior expert at McKinsey & Company, consulting with employers and payers on benefits design and delivery. Known for his deep industry relationships, strategic thinking, and operational excellence, Sondergeld is a trusted voice at the intersection of healthcare innovation, cost control, and access to care.