Director of Transportation Insurance

About the role

The Director of Transportation Insurance at Triumph is responsible for setting the vision and strategy for the company's Transportation Insurance division. This role involves overseeing the entire insurance lifecycle, from underwriting to claims, and launching a new Managing General Agent (MGA) to serve both large fleets and underserved small fleet trucking markets.

Responsibilities

• Define and execute the long-term strategy for Triumph's Transportation Insurance division
• Identify new markets, products, and partnerships
• Position Triumph as a leader in transportation risk management
• Oversee the full insurance lifecycle including underwriting, claims, and operations
• Establish Key Performance Indicators (KPIs) and drive operational excellence
• 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
• Expand distribution through multiple channels and partnerships
• Ensure adherence to all regulatory requirements, including transportation-specific regulations like the 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
• Represent Triumph at key industry events
• Develop high-performing teams across 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 a strong risk mindset
• Navigating complexity in a fast-moving environment
• Building trusted relationships internally and externally
• Developing high-performing teams

Skills

• Strategic thinking
• Financial discipline
• Risk management
• Complexity navigation
• Relationship building
• Team leadership

Benefits

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

Pay

TBD

Schedule

20–25% travel (industry events, client meetings, site visits)