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 Insurance

At 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 Do

Set the Vision & Strategy
You'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 Business
From 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 MGA
You'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 Expansion
You'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 & Governance
You'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 Industry
You'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 Teams
You'll lead a cross-functional organization spanning underwriting, claims, operations, compliance, and sales-fostering a culture of accountability, innovation, and continuous improvement.

What You Bring

• 10+ years of experience in commercial insurance, including 5+ years in senior leadership
• Deep expertise in transportation insurance (trucking liability, cargo, logistics)
• Proven experience owning and managing a P&L
• Track record of leading cross-functional teams across underwriting, claims, operations, and sales
• Strong knowledge of regulatory frameworks, including Federal Motor Carrier Safety Administration and state insurance laws
• Bachelor's degree required; MBA or advanced degree preferred
• Eligibility for Property & Casualty (P&C) insurance licensing
• Professional designations such as CPCU, ARM, or ARe are a plus

How You Lead

You're a strategic thinker who can also execute. You bring financial discipline, a strong risk mindset, and the ability to navigate complexity in a fast-moving environment. You build trusted relationships-internally and externally-and develop teams that consistently deliver results.

Additional Details

• Reporting to: Chief Revenue Officer
• Travel: ~20-25% (industry events, client meetings, site visits)

Why Triumph?

At Triumph, you'll have the opportunity to build-not just manage. You'll shape a new business, influence company strategy, and bring innovative solutions to an industry that's ready for change.

Apply now and take the next step in your career. We're excited to meet you!
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We offer Medical, Dental, Vision, Paid Time Off, 401k and much more.

Go on. Do it. Apply Today!