Director of Transportation Insurance

About the role

The Director of Transportation Insurance at Triumph is responsible for setting the vision and strategy for the transportation insurance division, scaling the business, launching and leading a Managing General Agent (MGA), guiding sales and market expansion, ensuring regulatory compliance, and developing high-performing teams.

Responsibilities

• Define and execute the long-term strategy for Triumph's Transportation Insurance division
• Identify new markets, products, and partnerships while positioning Triumph as a leader in transportation risk
• Oversee the full insurance lifecycle from underwriting to claims to operations
• Establish KPIs, drive operational excellence, and own the financial performance of the business, including P&L, forecasting, and cost management
• Leverage delegated authority, specialized underwriting expertise, and streamlined infrastructure to deliver faster, smarter insurance solutions
• Guide and develop a dedicated sales team, ensuring strong pipeline development and alignment with broader company priorities
• Expand distribution through multiple channels and partnerships
• Ensure adherence to all regulatory requirements, including transportation-specific regulations like Federal Motor Carrier Safety Administration
• Establish strong controls, manage risk, and serve as a key liaison to regulators, reinsurers, auditors, and executive leadership
• Build relationships with brokers, agents, carriers, and clients while representing Triumph at key industry events
• Develop insights that directly shape product development and go-to-market strategies
• Lead a cross-functional organization spanning underwriting, claims, operations, compliance, and sales

Requirements

• 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

Qualifications

• Strategic thinker with the ability to execute
• Financial discipline and strong risk mindset
• Navigates complexity in a fast-moving environment
• Builds trusted relationships internally and externally
• Develops high-performing teams

Skills

• Strategic thinking
• Financial discipline
• Risk management
• Team leadership
• Regulatory compliance
• Client engagement

Benefits

• Medical
• Dental
• Vision
• Paid Time Off
• 401k
• and much more

Pay

Competitive compensation package based on experience and qualifications.

Schedule

Full-time position with occasional travel (~20–25%) for industry events, client meetings, and site visits.