A Risky Future Webinar: Transportation, Captives, and Alternative Markets

Overview

Hosted by Insurance Journal’s Andrea Wells, this webinar dives into the urgent challenges facing fleet insurance today, exposing the mounting pressures on trucking companies and the growing shift toward alternative risk solutions like captives. Industry experts will reveal why traditional insurance markets are becoming unsustainable, the game-changing advantages of captives, and the critical partnerships needed for success.

They’ll also uncover hidden roadblocks—like regulatory concerns and exit strategies—and provide a bold look into the future of fleet insurance, where captives could reshape the industry as we know it.

What You Will Learn //

• Current Market Challenges – Why insuring trucking fleets has become more difficult and how claims trends are impacting the industry.
• Alternative Risk Solutions – How captives and other alternative markets work, their benefits, and the key factors for success.
• Strategic Partnerships & Considerations – The role of TPAs, brokers, and captive managers in ensuring a well-run program, plus key roadblocks to be aware of when exploring alternatives.

Panelists //

Garrett Yates
VP at Heffernan Insurance Brokers

Garrett Yates is the Vice President at Heffernan Insurance Brokers. His specialties include risk management, professional liability, and captive insurance for middle market/large commercial clients. Garrett’s focus niches include trucking, financial institutions, manufacturing, surety, and construction-related businesses. When he’s not creating solutions for insurance programs, you can find him traveling with his wife, spending time with his beautiful grandchildren, or on a boat fishing and enjoying the great outdoors!

Kenny Planeta
Transportation Practice Leader at Heffernan Insurance Brokers

Kenny Planeta is an experienced insurance professional, currently serving as the Senior Vice President and Transportation Practice Leader at Heffernan Insurance Brokers. With a diverse background in commercial insurance, finance, and DOT compliance, Kenny brings a unique blend of expertise to his role.

Known for his exceptional ability to understand client needs and build strong relationships, Kenny has a proven track record of expanding into new areas and creating business opportunities. His hands-on experience in insurance sales, finance, management, and underwriting reflects his dedicated and focused approach to success in the industry.

Cheri McGonagill-Spann, CPCU, CCP, Transportation-Certified Paralegal
Nat’l Transportation & Cargo Product Manager at Crawford and Company

Cheri McGonagill has dedicated over twenty years to a remarkable career in commercial transportation. She exemplifies dedication and expertise with a specialization in Motor Truck and Cargo Liability.

Cheri, a certified paralegal, holds a bachelor’s degree in business administration from Arizona State University. As a Certified Transportation Professional in Claims and a CPCU designee, she embodies the pursuit of excellence. Her recent achievement of a Negotiations, Mediations, and Alternative Dispute Resolution Certification from Harvard Law Program showcases her commitment to growth.

Cheri’s journey has been marked by diverse experiences that enrich her perspective. She has worked as an adjuster, taken those 2 AM callouts, served as a claims manager for a medium-sized trucking company, worked for an insurer desk, and worked as a field IA. Her interactions with law enforcement, trucking companies, vendor partners, and defense and plaintiff attorneys have given her a broad perspective and adaptability that reassure her readiness to learn and contribute.

Cheri’s commitment to personal growth and education is unwavering. Her continuous pursuit of knowledge and skills not only benefits her but also inspires those around her. As a passionate advocate for the transportation industry, particularly in the realm of education, she leads by example, showing that the journey of improvement is a lifelong one.

David Hoag
Assistant Vice President, Business Development Manager – U.S. Loss Adjusting / Business Development at Crawford & Company

At Crawford & Company, David Hoag’s emphasis on business development and account management has strengthened the company’s status as a leader in loss adjusting. His team’s dedication to excellence has led to the establishment of strategic partnerships and improved client service throughout the Western U.S.

With several years of committed service in the insurance and restoration sectors, David specializes in navigating intricate sales processes and broadening the company’s market presence. His leadership and deep understanding of client needs form the foundation of his approach, ensuring that Crawford & Company’s managed repair and catastrophe response solutions consistently meet customer expectations. The organization’s growth reflects the collective efforts of David and his team in providing outstanding service and nurturing lasting industry relationships.