Bio
Caleb Pearson is a transformative leader with 20 years of experience in corporate strategy and relationship-driven growth. As Vice President of Strategic Growth at Hill and Stone Insurance, he focuses on building long-term partnerships and delivering tailored risk solutions for successful individuals, families, and businesses.
Drawing on executive leadership roles across Fortune 500 companies, Caleb elevates the client experience, expands advisory capabilities, and drives sustainable growth through personalized service and trusted guidance.
Before transitioning into insurance, Caleb served as Vice President at McDonald’s, where he led Media, CRM, Loyalty, Digital, Delivery, and Customer Experience—managing a $1B+ budget and a team of over 250. Earlier in his career, he led Marketing Strategy and Analytics at Grubhub and held leadership roles at Citi, specializing in loyalty marketing for affluent clients.
Caleb holds a BS from Wake Forest University and an MBA from Georgetown University. He has completed the Chicago and Tokyo Marathons in support of Ronald McDonald House Charities. Known for his integrity, thoughtful leadership, and ability to build high-performing teams, he consistently earns the trust of clients and colleagues alike. He lives in Lake Bluff, Illinois, with his wife Natalie—who leads their family insurance firm—and their three daughters: Penelope, Lilyrose, and Miley. Outside of work, he enjoys international travel, golf, and live music.
