Director of Transportation Insurance

Join Triumph!At Triumph, our vision is a world where freight transactions are accurate and seamless on the most modern and secure freight transaction network. That’s why we’re looking for passionate, innovative, solutions-oriented people to join our team. We thrive on providing exceptional customer service and we look for team members with an entrepreneurial spirit and a passion to build successful partnerships with our clients. Because at the end of the day our goal is to help our partners businesses run better.Director of Transportation InsuranceAt Triumph, we’re building something different—modern financial and technology solutions purpose-built for the transportation industry. We’re looking for a Director of Transportation Insurance to lead and scale a critical growth area of our business.This is a rare opportunity to stand up and lead a specialized insurance division, including the launch of a purpose-built Managing General Agent (MGA), designed to serve both large fleets and the underserved small fleet trucking market.What You’ll DoSet the Vision & StrategyYou’ll define and execute the long-term strategy for Triumph’s Transportation Insurance division—identifying new markets, products, and partnerships while positioning Triumph as a leader in transportation risk.Build and Scale the BusinessFrom underwriting to claims to operations, you’ll oversee the full insurance lifecycle. You’ll establish KPIs, drive operational excellence, and own the financial performance of the business, including P&L, forecasting, and cost management.Launch and Lead an MGAYou’ll lead the development and launch of a modern MGA—leveraging delegated authority, specialized underwriting expertise, and streamlined infrastructure to deliver faster, smarter insurance solutions.Lead Sales & Market ExpansionYou’ll guide and develop a dedicated sales team, ensuring strong pipeline development and alignment with broader company priorities. You’ll also help expand distribution through multiple channels and partnerships.Own Risk, Compliance & GovernanceYou’ll ensure adherence to all regulatory requirements, including transportation-specific regulations like Federal Motor Carrier Safety Administration. You’ll establish strong controls, manage risk, and serve as a key liaison to regulators, reinsurers, auditors, and executive leadership.Engage Clients & the IndustryYou’ll build relationships with brokers, agents, carriers, and clients while representing Triumph at key industry events. Your insights will directly shape product development and go-to-market strategies.Develop High-Performing TeamsYou’ll lead a cross-functional organization spanning underwriting, claims, operations, compliance, and sales—fostering a culture of accountability, innovation, and continuous improvement.What You Bring10+ years of experience in commercial insurance, including 5+ years in senior leadershipDeep expertise in transportation insurance (trucking liability, cargo, logistics)Proven experience owning and managing a P