Dennis Jolley
Healthcare Strategy in an Era of Uncertainty: Dennis Jolley on Trust, AI & Leading Through Change
Dennis Jolley
President, SHSMD

Healthcare Strategy in an Era of Uncertainty: Dennis Jolley on Trust, AI & Leading Through Change

With Dennis Jolley
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I recently had the pleasure of catching up with my old friend and repeat podcast guest Dennis Jolley, System Vice President, Strategy and Planning at UW Health and current President of SHSMD.

We talked about the vital role of strategy in health systems, what’s keeping hospital leaders up at night, and how they’re navigating what may be one of the most rapidly changing healthcare environments any of us can remember.

Dennis has a great way of describing it. At UW Health, he uses a “Trend Radar” with the board and senior leadership to track the forces affecting the organization. This year, he told them he had never seen the radar this messy. Instead of one or two areas creating disruption, virtually everything is moving at once—from workforce shortages and financial pressures to policy changes, AI, consumer expectations, access, and declining public trust.

But this isn’t a conversation about doom and gloom. Dennis and I explored how smart health systems are responding: bringing strategy, marketing, communications, physician relations, business development, and operations together; finding practical uses for AI; reducing friction for patients; and making difficult choices about growth, access, and financial sustainability.

Our conversation is also a great preview of what healthcare leaders can expect at the SHSMD Connections Annual Conference, September 27–29 in Baltimore—particularly Dennis’s argument that healthcare’s “strategy disciplines” need to get outside their individual silos and learn from one another.

Why Listen?

In this episode, Dennis and I discuss:

  • Why health system leaders are facing an unusually complex convergence of financial, workforce, policy, access, and consumer pressures.
  • Why marketing, communications, physician relations, business development, and strategy need to be at the table together, rather than brought in after strategic decisions have already been made.
  • Where AI is already reducing friction for patients—from wayfinding and prescription management to clinical workflows.
  • Why growth increasingly means getting the right patient to the right place at the right time, while still generating the margins necessary to support a health system’s broader mission.
  • Why trust has become a strategic issue for healthcare organizations—and why better communications alone won’t solve it.
  • What CEOs increasingly expect from their marketing and strategy leaders: come to the table with solutions, not problems.

Key Insights and Takeaways

  1. Strategy is a team sport. Dennis jokes that he isn’t an “evil genius who sits in a cave and comes up with the strategy for the health system.” His job is to convene smart people, ask questions, connect perspectives, and find a way forward. That same principle applies across marketing, communications, physician relations, business development, and operations.
  2. AI’s immediate opportunity is often surprisingly practical. While much of the industry debates AI at a grand scale, Dennis points to applications that solve everyday problems: helping patients navigate enormous hospital campuses, summarizing medical records, managing prescriptions, reminding patients about labs, and making healthcare easier to use.
  3. Growth and mission aren’t opposites. Health systems need profitable services to generate the margin that helps support essential services that may never reimburse adequately. The strategic question is how to grow while delivering the right care to the right patients and preserving the organization’s broader community mission.

4. Trust has become a strategic asset. Dennis readily admits there is no simple answer to healthcare’s growing trust deficit. But transparency, community engagement, easier patient experiences, and consistently demonstrating value all matter.

5. Executives want solutions. Dennis hears the same message from CEOs repeatedly: “Come with solutions. Come with ideas. Come to the table.” Marketing and strategy leaders who understand what matters to the CEO—and bring ideas for solving those problems—become far more valuable to the organization.

“Come with solutions. Come with ideas. Come to the table.”
Dennis Jolley

Dennis Jolley

President, SHSMD

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Note: The following AI-generated transcript is provided as an additional resource for those who prefer not to listen to the podcast recording. It has been lightly edited and reviewed for readability and accuracy.

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