Director of Risk & Insurance

CrossCountry Freight Solutions•Eagan, MN

5d•$125,000 - $150,000•Onsite

About The Position

The Director of Risk & Insurance is a senior leadership role responsible for developing and executing CrossCountry Freight Solutions’ enterprise insurance strategy, managing corporate risk controls, and overseeing legal loss prevention and mitigation. This role serves as the company’s primary subject matter expert on insurance structure, coverage adequacy, captive management, and large or complex claims escalation. Reporting directly to the CFO, the Director of Risk & Insurance will work collaboratively with HR, Legal, Compliance, Operations, and external brokers and carriers to ensure the company’s risk posture is properly structured, adequately insured, and strategically managed. A key objective of this role is the ongoing reduction of the company’s Total Cost of Risk (TCOR) through disciplined claims management, strategic insurance placement, loss control initiatives, and enterprise risk mitigation. This role has escalation authority and strategic oversight responsibility for claims with a reserve or exposure at or above the defined threshold established by the CFO, working in coordination with the Sr. Director of Compliance who retains day-to-day claims management responsibility.

Requirements

Bachelor’s degree in Risk Management, Finance, Business Administration, or related field required; advanced degree or professional designation (ARM, CPCU, RIMS-CRMP) preferred.
Minimum 10 years of progressive experience in insurance, risk management, or a related field; transportation or logistics industry experience strongly preferred.
Demonstrated experience managing captive insurance programs required.
Experience managing large commercial insurance programs with multi-line coverage structures required.
Expert-level knowledge of commercial insurance products, coverage structures, and policy language across auto liability, cargo, workers’ compensation, general liability, and excess/umbrella lines.
Strong understanding of captive insurance mechanics, including fronting arrangements, reinsurance, loss portfolio transfers, and domicile regulatory requirements.
Knowledge of transportation regulatory environment including FMCSA, DOT, and motor carrier insurance filing requirements (MCS-90, BMC-91).
Exceptional analytical, negotiation, and communication skills; ability to present complex insurance concepts clearly to non-insurance audiences.
Experience working with outside legal counsel on litigation strategy and claim resolution.
Proficiency in Microsoft Office Suite; experience with risk management information systems (RMIS) preferred.

Responsibilities

Insurance Structure, Products & Strategy Develop, maintain, and execute the company’s enterprise insurance strategy across all lines of coverage including auto liability, general liability, cargo, workers’ compensation, excess/umbrella, and D&O.
Manage the company’s captive insurance program including structure, funding, governance, claims reserving, and relationship with captive managers and domicile regulators.
Lead annual insurance renewal process including coverage analysis, market evaluation, broker negotiations, and executive presentation of recommendations.
Evaluate coverage adequacy against the company’s risk profile on an ongoing basis; identify gaps or exposures and recommend adjustments.
Manage relationships with insurance brokers, carriers, reinsurers, and risk management consultants.
Oversee the company’s third-party administrator (TPA) relationships and internal claims management structure; ensure appropriate service levels, reporting, and accountability across all TPA partners; provide strategic oversight and escalation management for complex or high-exposure claims in coordination with the Sr. Director of Quality, Risk & Compliance.
Corporate Risk Management & Controls Design and implement the company’s enterprise risk management framework, identifying, assessing, and prioritizing operational, financial, regulatory, and reputational risks.
Develop and maintain risk registers, escalation protocols, and risk reporting dashboards for executive and board-level review.
Partner with Operations, Safety, HR, and Finance to embed risk controls into business processes across the organization.
Monitor industry trends, regulatory changes, and loss benchmarks to proactively adjust the company’s risk management posture.
Conduct periodic risk assessments of new business initiatives, acquisitions, or structural changes including owner-operator program evaluations.
Corporate Legal Loss Prevention & Mitigation Oversee the company’s legal loss prevention strategy, working closely with outside counsel and internal stakeholders to minimize litigation exposure.
Develop and implement pre-litigation resolution strategies and coordinate defense posture on active matters.
Partner with HR and Compliance on high-exposure employment claims, ensuring appropriate legal strategy is engaged early.
Maintain awareness of nuclear verdict trends, venue risk, and jurisdictional exposure relevant to LTL trucking operations; advise leadership accordingly.
Identify systemic patterns in legal claims and losses and recommend operational or policy changes to reduce recurrence.
Large Loss Escalation & Strategic Claims Oversight Serve as the escalation authority for all claims with a reserve or potential exposure at or above the threshold established by the CFO.
Direct strategy and provide decision-making authority on claim file reviews, mediations, and depositions for all matters at or above the escalation threshold; the Sr. Director of Quality, Risk & Compliance retains lead responsibility for day-to-day claims activity and initial file management below the threshold, with a clear handoff to this role upon escalation trigger.
Provide strategic direction on coverage positions, settlement authority, and litigation posture for escalated claims.
Engage and coordinate with legal counsel on all escalated, high-exposure, or complex matters; direct defense strategy, manage litigation spend, and ensure timely communication of legal developments to the CFO and executive leadership.
Establish and maintain a formal escalation protocol in collaboration with the Sr. Director of Compliance defining trigger criteria, notification timelines, and decision rights for large or complex claims.
Report to CFO and executive leadership on large loss activity, reserve adequacy, and trends affecting the company’s overall loss picture