DOUGLAS L RUTTER

Douglas L. Rutter

Founder, Chairman & Chief Executive Officer

Leadership built through discipline, vision, and an unwavering commitment to long-term stewardship.

Douglas L. Rutter founded The Rutter Organization in 1988 with a simple philosophy: build lasting value through integrity, disciplined execution, and trusted relationships. Over nearly four decades, he has grown the organization into a diversified enterprise spanning tax services, private investments, real estate, media, and historical preservation.

With a background in finance, accounting, and business operations, Doug has advised thousands of individuals, families, and businesses while building organizations designed to endure. His leadership emphasizes strategic thinking, responsible capital allocation, operational excellence, and sustainable long-term growth.

Beyond business, Doug is the creator and host of The Rebound 915 Podcast and founder of From the Rutter Collective, preserving the people, moments, and artifacts that have shaped sports, entertainment, and American culture. Through these platforms, he is committed to documenting history, celebrating achievement, and strengthening the communities that have influenced his life’s work.

Leadership Focus: Strategic Leadership • Tax Advisory • Private Investments • Media • Historical Preservation

Jessica Truly

Vice President of Operations & Client Services

Operational excellence built through discipline, precision, and exceptional service.

Jessica Truly serves as Vice President of Operations & Client Services for The Rutter Organization, providing the operational leadership that keeps every division aligned, efficient, and client-focused. She oversees organizational systems, workflow management, service standards, and cross-functional coordination, ensuring every client experience reflects the professionalism and responsiveness that define the organization.

Working closely with executive leadership, Jessica transforms strategy into disciplined execution while fostering a culture of accountability, collaboration, and continuous improvement. Her leadership strengthens operational performance, supports sustainable growth, and reinforces the trusted relationships that have defined The Rutter Organization since 1988.

Leadership Focus: Operations • Client Experience • Organizational Systems • Process Improvement