JOSH MCKENNA
CHIEF OPERATING OFFICER
JOSH MCKENNA
CHIEF OPERATING OFFICER
ABOUT JOSH
Josh McKenna is Chief Operating Officer and Partner at Caliber Wealth Management. He leads the firm’s operating platform — aligning people, process, technology, and culture to support sustainable growth and an exceptional client experience.
Josh works at the intersection of strategy and execution. He helps translate long-term vision into real systems: scaling advisor support, integrating acquisitions, strengthening leadership infrastructure, and modernizing the firm’s operating model in an AI-driven financial services landscape. His focus is simple: build a business that is both human-centered and operationally excellent.
With over 20 years of experience in organizational development and business operations, Josh has helped multiple companies move from growth chaos to clarity, consistency, and momentum. At Caliber, he partners closely with ownership and leadership to keep the firm focused on its highest-impact priorities while continuously improving how the business actually runs.
After his early years in Southern California, Josh grew up in Overland Park and went on to attend KU. He and his wife Rachel have been married for over 25 years and are raising 5 kids. He’s drawn to fly fishing, yoga, good books (currently Middlemarch), and conversations with people who want to grow, think deeper, and move forward with vision and purpose.
Raymond James and its advisors do not offer tax or legal advice. You should discuss any tax or legal matters with the appropriate professional.