About The Position

At Triumph, the Director of Transportation Insurance will lead and scale a critical growth area of the business, specifically a specialized insurance division. This role involves launching a purpose-built Managing General Agent (MGA) designed to serve both large fleets and the underserved small fleet trucking market. The company seeks passionate, innovative, and solutions-oriented individuals with an entrepreneurial spirit to build successful partnerships and help clients' businesses run better.

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
  • Eligibility for Property & Casualty (P&C) insurance licensing

Nice To Haves

  • MBA or advanced degree preferred
  • Professional designations such as CPCU, ARM, or ARe are a plus

Responsibilities

  • 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.
  • 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.
  • Lead the development and launch of a modern MGA—leveraging 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.
  • Help 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.
  • Directly shape product development and go-to-market strategies through insights.
  • Lead a cross-functional organization spanning underwriting, claims, operations, compliance, and sales—fostering a culture of accountability, innovation, and continuous improvement.

Benefits

  • Medical
  • Dental
  • Vision
  • Paid Time Off
  • 401k
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