Doug Shepson is a seasoned executive, insurance professional, risk-management advisor, and organizational leader whose career spans more than three decades across commercial insurance, education, legal services, behavioral healthcare, and leadership development. Throughout his professional journey, he has built a reputation around helping people and organizations recognize challenges, manage risk, strengthen operations, and pursue sustainable growth. His leadership philosophy centers on empowering teams, fostering accountability and collaboration, delivering meaningful value to customers and stakeholders, and creating environments where people have opportunities to develop and succeed. Whether advising a business owner, leading an insurance office, developing professionals, or educating students, Doug brings a practical, relationship-driven perspective to leadership.
Doug currently serves as Senior Vice President with Brown & Brown of Indiana, continuing a long and progressive career with Brown & Brown that began in 2007. His advancement from Commercial Sales Executive to Executive Vice President and ultimately Senior Vice President reflects extensive experience in both client-facing commercial insurance and executive leadership. Across assignments in Florida, Michigan, and Indiana, he has been responsible for office leadership, operational decision-making, sales management, customer service, budgeting, staff development, and the delivery of insurance and risk-management solutions. This combination of executive responsibility and direct client engagement has given Doug a broad understanding of how organizational strategy ultimately translates into operational execution and customer value.
Risk management and commercial insurance have been central to Doug’s work for nearly two decades. He has advised business owners and community associations on insurance programs designed to protect assets, address exposures, and support organizational continuity. His experience encompasses workers’ compensation, property, general liability, professional liability, commercial automobile, crime, inland marine, umbrella, flood, Directors and Officers liability, employment practices liability, and other commercial coverage areas. Rather than viewing insurance simply as a financial product, Doug approaches it as one component of a broader risk-management strategy—one that requires understanding an organization’s people, operations, assets, responsibilities, and long-term objectives.
Doug’s leadership responsibilities have extended well beyond insurance placement. As an Executive Vice President in Brown & Brown offices in Ocala, Florida, and Fenton, Michigan, and later in Indianapolis, Indiana, he has managed the practical realities of running and growing business operations. His responsibilities have included leading sales and service teams, overseeing budgets, addressing customer needs, supporting staff, and making day-to-day operating decisions aligned with broader organizational goals. These experiences have strengthened his ability to evaluate challenges from multiple perspectives and balance strategic priorities with the realities of execution. They have also given him significant exposure to the concerns that occupy business owners and senior executives, including growth, workforce performance, financial protection, customer relationships, organizational resilience, and risk.
His experience working closely with owners and executives is particularly relevant to his interest in board and advisory service. Doug understands that strong governance requires more than identifying risk; it requires asking thoughtful questions about how risk connects with strategy, operations, people, reputation, and long-term organizational health. His familiarity with Directors and Officers liability and related executive risks provides an additional perspective on the responsibilities carried by directors and organizational leaders. He can contribute practical insight into areas such as insurance strategy, liability oversight, business continuity, contractual risk, workforce exposures, and the protection of organizational assets while maintaining an appreciation for the broader strategic objectives of the enterprise.
Doug’s professional foundation is unusually diverse and contributes to the perspective he brings to executive leadership. Before entering commercial insurance, he worked in higher education and leadership development, including serving as a Visiting Assistant Professor of Christian Ministries at Trinity International University. Earlier, at Wheaton College / HoneyRock, he spent nearly a decade working with undergraduate students through educational programming, leadership development, curriculum creation, marketing, and outdoor experiential learning. These roles sharpened his ability to teach, mentor, communicate, and develop others—capabilities that later became valuable in managing professionals and building effective teams.
Earlier chapters of Doug’s career provided additional exposure to the legal and healthcare environments. As a Legal Assistant with Blatt, Hammesfahr & Eaton in Chicago, he supported case management, legal research, trial preparation, deposition analysis, and document-management processes. Prior to that, his work with Carle Pavilion included responsibilities as an Assessment Specialist and Mental Health Technician, where he worked in behavioral-health settings supporting individuals with psychiatric, behavioral, and chemical-dependency needs. Together, these experiences broadened his understanding of documentation, process discipline, human behavior, healthcare environments, and the importance of careful decision-making when organizations and individuals face difficult circumstances.
Doug’s academic and professional development reflects the same multidisciplinary approach. He earned a Bachelor of Science in Psychology and History from the University of Illinois Urbana-Champaign, completed the graduate-level ABA-approved Lawyers Assistant Program at Roosevelt University, and earned a Master of Arts in Educational Ministries from Wheaton College. Within the insurance profession, he holds the Certified Insurance Counselor (CIC) designation and has held licenses spanning property and casualty, life, accident and health, and surplus lines insurance. This blend of education, professional certification, operational experience, and interpersonal expertise enables him to approach organizational challenges through multiple lenses rather than relying on a single discipline.
From an industry perspective, Doug brings particularly relevant knowledge to organizations operating in insurance, risk management, manufacturing, construction, healthcare, education, and other environments where operational complexity and liability exposures require disciplined oversight. His commercial insurance career has placed him alongside business owners as they evaluate how to protect assets while continuing to grow. That vantage point has allowed him to observe recurring challenges across organizations and industries, including workforce risk, property exposures, contractual obligations, liability management, continuity planning, and the relationship between operational decisions and financial consequences. His experience makes him comfortable engaging with both strategic questions and the practical details necessary to turn decisions into action.
Doug is actively pursuing board opportunities as a way to give back to organizations and communities while applying the experience accumulated throughout his career. He is particularly interested in contributing his knowledge of risk management, insurance, operations, leadership, and organizational development to boards navigating growth, change, or increasingly complex risk environments. He views board service as an opportunity to support management thoughtfully, strengthen organizational resilience, and contribute perspective developed from decades of working with executives, business owners, employees, students, and professionals from a variety of backgrounds.
Beyond his professional life, Doug values service, personal development, community, and exploration. His interests include nonprofit involvement, outdoor activities, wilderness backpacking, and camping. He holds a private pilot’s license and a SCUBA diving certification, and his travels have taken him throughout the United States and Canada as well as South America, Europe, Australia, New Zealand, China, Haiti, and Jamaica. He has also maintained an ongoing commitment to his local church. These interests reflect an enduring curiosity about people and places as well as a willingness to learn through experience—qualities that complement his professional commitment to developing people and building trusted relationships.
At the center of Doug’s professional philosophy is a belief that sustainable success comes from combining disciplined leadership with genuine investment in people. He seeks to build organizations where accountability and collaboration coexist, where customer and stakeholder relationships are treated as long-term commitments, and where teams understand both what they are trying to accomplish and why it matters. His career demonstrates a consistent progression from serving individuals and developing emerging leaders to advising business owners and ultimately leading complex commercial insurance operations. As he expands his involvement in board and advisory service, he brings a perspective grounded in risk awareness, operational leadership, relationship building, and a commitment to helping organizations and their people succeed.
Character:
Doug approaches leadership with accountability, service, integrity, and a sustained commitment to developing people and building trusted relationships. His professional and personal experiences demonstrate a willingness to take responsibility, invest in others, and contribute his expertise in ways that create lasting value for organizations and communities.
Knowledge:
Combining deep commercial insurance and risk-management knowledge with experience spanning operations, education, legal services, behavioral healthcare, and leadership development. His Certified Insurance Counselor designation, professional licenses, multidisciplinary education, and decades of professional experience give him a broad foundation from which to understand organizational exposures and business challenges.
Strategic:
Doug connects risk management with larger questions of growth, operational resilience, asset protection, workforce performance, and organizational continuity. His experience leading offices, managing budgets and teams, advising business owners, and designing risk-management programs enables him to consider both the strategic implications of decisions and the operational requirements needed to execute them successfully.
Communication:
His career has consistently required him to translate complex subjects into practical guidance for clients, employees, students, executives, and business owners. His background as an educator, advisor, sales executive, and senior organizational leader has strengthened his ability to listen carefully, communicate clearly, develop relationships, and engage diverse stakeholders around shared objectives.
