In this episode, we sit down with Greg Conner, CFO of Trilogy Health Services, to explore his journey from banking in Chicago to executive leadership in one of the Midwest’s leading senior living organizations. Greg shares how Trilogy is redefining senior care through integrated campuses, why culture drives execution more than strategy alone, and how servant leadership shapes decision-making at every level of the organization.

What You’ll Learn:

• How Trilogy Health Services operates across skilled nursing, assisted living, memory care, and independent living on integrated campuses.
• Why moving seniors—especially those with dementia—can significantly impact health outcomes.
• What Greg learned from navigating the 2008 financial crisis and working through multiple banking roles.
• Why job-hopping is common in banking and how relationship-driven careers evolve in the industry.
• How to make yourself indispensable by solving problems others avoid.
• The difference between management, leadership, and executive responsibility in modern organizations.
• Why servant leadership flips the traditional corporate structure upside down.
• How culture and strategy work together to drive outcomes in healthcare organizations.
• Greg’s perspective on long-term growth in senior healthcare as demographics shift in the U.S.

This episode is perfect for leaders, operators, and professionals interested in healthcare leadership, finance, organizational culture, and career growth, especially those looking to understand how high-performing teams scale while staying mission-driven.