Win Via Trust Leadership Podcast Pearls: The Chief Medical Officer for Millions

How Trust Scales Healthcare, Insights from Dr. Harry Leider

In this episode of the Win Via Trust podcast, Michael Rabinowitz speaks with Dr. Harry Leider, a physician executive whose career spans Walgreens, biotech startups, Harvard Medical School, digital health innovation, and decades of leadership at the intersection of medicine and business. Harry’s journey illustrates how trust becomes the essential force behind meaningful impact in healthcare.

From an early age, Harry was drawn to science and problem solving. “Science, and puzzles is what being a doctor is all about,” he notes. His interest in leadership emerged in college, where he discovered the power of building teams and multiplying what one person can accomplish. That insight eventually led him to the Robert Wood Johnson Clinical Scholars Program, where he combined public health training with an MBA. The idea was simple, yet transformative. A physician may touch thousands of lives, but with the right platforms, a leader can touch millions.

The Mentorship That Shaped His Leadership

Despite his extensive training, Harry acknowledges that he entered leadership as a novice. Early in his career, he learned that expertise alone does not make a leader. “You cannot tell professionals what to do, especially those with more experience than you,” he recalls. A seasoned mentor helped him understand that leadership requires humility, influence, and a commitment to developing new skills. This became a foundation for the rest of his career.

What Trust Means in Healthcare

Harry draws a clear distinction between trust in business and trust in healthcare. In most industries, trust enables collaboration. In healthcare, trust protects lives. “If you do not have trust, people could get hurt. People might not have a good outcome.” Whether the work involves biopharma, digital health, telemedicine, or consumer apps, trust determines whether patients engage, adopt, and benefit.

The Power of a Trusted Brand

During his tenure as Chief Medical Officer at Walgreens, Harry helped guide one of America’s most iconic healthcare brands. Walgreens benefited from more than a century of community presence and from the unique trust consumers place in pharmacists. As Harry explains, a diabetic may visit a pharmacy a dozen times a year, while seeing a physician only twice. Walgreens used this trust to expand into clinics, vaccinations, and digital health long before these services became mainstream.

Digital Health Before It Was Mainstream

In 2015, Harry helped launch Walgreens’ first digital health and telemedicine platform. The partnership with MDLive allowed Walgreens to offer virtual visits through an app already used by millions of consumers. He also helped design one of the earliest behavior based engagement programs, rewarding users for steps, weigh ins, and other healthy activities. These efforts became early models for today’s digital wellness ecosystems.

The Real Barrier in Digital Health

Harry is direct about the biggest challenge in digital health. Engagement, not technology. “Only 15 percent of people will use it, and that is a high number.” When the program is offered by a trusted physician, engagement can rise to 50 or 60 percent. Trust, not design or incentives, is the multiplier.

Trust as a Filter for Choosing Partners

In his current work, Harry advises emerging healthcare companies as a fractional Chief Medical and Strategy Officer. The model allows him to support several innovators while giving each one access to senior clinical leadership.

That flexibility also requires careful judgment. Harry shared an example of a company developing a digital diagnostic tool. Once he reviewed the underlying data, the evidence did not support the claims being made, which led Harry to step away. Protecting his reputation, and the trust associated with it, mattered more than the engagement.

It is a clear reminder that trust guides not only how leaders act, but also who they choose to work with.

AI in Healthcare

Harry sees significant potential for AI in administrative and back office functions, including transcription, claims, and record assembly. When it comes to diagnosis and treatment, he believes AI must remain under professional supervision. He has personally caught AI hallucinations while reviewing medical literature, including instances where AI cited studies that did not exist. AI can accelerate clinicians, but it cannot replace them.

Final Advice for Leaders

Harry leaves listeners with two ideas. First, Adam Grant’s book Give and Take, which argues that being a giver, with boundaries, is the most effective long term leadership style. Second, his own framework. Ideas generate interest, evidence generates trust, and trust enables scale. This is the path to building any organization, especially in healthcare.