Manager, Transportation and Risk Compliance

Our freight brokerage client in the greater Chicago area is looking for a Manager, Transportation and Risk Compliance! JOB SUMMARY The Manager, Transportation Risk & Compliance is responsible for overseeing transportation risk and compliance across the organization’s brokerage and asset based operations. This role serves as the primary internal owner for carrier compliance and onboarding standards, fleet safety and DOT compliance, the company’s insurance program, claims coordination, and customer and contractual compliance requirements. The Manager, Transportation Risk & Compliance will work closely with Operations, Carrier Sales, Fleet Operations, Human Resources, Accounting, Executive Leadership, insurance brokers, and outside counsel to ensure requirements are clearly understood, documented, communicated, and followed throughout the organization. This is a hands on role requiring someone who understands transportation operations and can translate regulatory, insurance, and contractual requirements into practical processes and procedures. PRIMARY RESPONSIBILITIES Carrier Compliance & Onboarding Develop and own KLFM’s technology strategy and multi-year technology roadmap aligned with the company’s operational priorities, growth objectives and long-term vision. Assess the current technology environment and define the capabilities necessary to support the future-state organization. Own carrier onboarding, qualification, and ongoing monitoring procedures across all brokerage entities. Establish and maintain carrier qualification standards including operating authority, insurance, safety history, authority age, fraud indicators, and customer specific requirements. Ensure carrier qualification documentation is complete, accurate, and maintained appropriately. Own and maintain Do Not Use criteria and carrier exception and approval procedures. Monitor changes to carrier authority, safety, insurance, and compliance status and ensure appropriate action is taken. Oversee carrier insurance verification and ensure required coverage remains current. Identify and implement controls designed to reduce carrier fraud and cargo theft exposure. Conduct periodic audits of carrier onboarding and qualification practices. Develop, maintain, and communicate carrier compliance SOPs. Provide training and guidance to Carrier Sales and Operations regarding carrier compliance requirements. Serve as the primary escalation point for carrier qualification and compliance concerns. Fleet Safety & DOT Compliance Oversee DOT and FMCSA compliance for the organization’s asset based transportation entities. Maintain compliant and audit ready Driver Qualification Files. Oversee CDL, medical certification, MVR, FMCSA Clearinghouse, drug and alcohol testing, and driver qualification requirements. Monitor Hours of Service and ELD compliance. Monitor CSA/SMS performance, roadside inspections, violations, and related corrective actions. Ensure vehicle inspection, maintenance, registration, permitting, and required compliance records are properly maintained. Coordinate DOT and FMCSA audits, compliance reviews, and regulatory inquiries. Oversee required driver safety orientation and ongoing compliance training. Review accidents and safety incidents and ensure appropriate documentation, investigation, reporting, and corrective action. Partner with Operations and Human Resources on driver safety and compliance matters. Insurance & Claims Serve as the primary internal owner of the company’s insurance program across all entities. Manage the day to day relationship with the company’s insurance broker and coordinate communication between the broker and internal stakeholders. Coordinate annual insurance renewals and the collection and submission of required underwriting and exposure information. Maintain a centralized schedule of insurance policies, coverage limits, deductibles, renewal dates, covered entities, and significant exclusions or requirements. Coordinate Certificates of Insurance and customer specific insurance requests. Review customer insurance requirements and identify requirements that exceed or conflict with existing coverage. Coordinate insurance requirements and coverage integration for acquisitions, new entities, and changes in operations. Coordinate insurance audits and ensure required information is provided accurately and timely. Coordinate reporting and management of cargo, auto, general liability, cyber, and other insured claims. Maintain centralized records of open claims and monitor claims through resolution. Identify recurring loss trends and work with leadership and operational teams to reduce future exposure. Escalate significant coverage questions, exclusions, uninsured exposures, or potential gaps to Executive Leadership, the insurance broker, or outside counsel as appropriate. Customer & Contract Compliance Review new and existing customer requirements to identify operational, safety, insurance, and compliance obligations. Review customer contracts from an operational risk and compliance perspective. Identify contractual provisions requiring additional review by Executive Leadership, the company’s insurance broker, or outside counsel. Maintain a centralized record of significant customer specific requirements including insurance limits, cargo requirements, carrier qualifications, tracking requirements, security protocols, and other operational obligations. Partner with Sales and Operations to confirm the organization can meet customer requirements before commitments are made. Coordinate completion of customer safety, compliance, and insurance questionnaires. Develop and maintain customer specific compliance procedures when required. Conduct periodic reviews to confirm continued adherence to significant customer contractual and operational requirements. Policies, Audits & Risk Management Develop, maintain, and continuously improve transportation safety, risk, and compliance policies and SOPs. Ensure compliance procedures are consistently applied across business units and entities. Maintain organized and audit ready compliance documentation. Conduct periodic internal compliance audits and ensure identified deficiencies are corrected. Monitor changes to DOT, FMCSA, and other applicable transportation regulations and communicate relevant changes to the organization. Proactively identify areas of operational, regulatory, and insurance risk and recommend appropriate controls. Partner with leadership to establish appropriate approval and escalation procedures for compliance exceptions and significant risk. Develop and maintain meaningful safety, compliance, claims, and risk reporting for Executive Leadership. MEASURES OF SUCCESS Consistent carrier onboarding and qualification procedures across all brokerage entities. Complete and audit ready fleet and driver compliance records. Timely identification and resolution of carrier, fleet, insurance, and customer compliance issues. Clear ownership and organization of the company’s insurance program across all entities. Accurate and timely insurance renewals, audits, claims reporting, and customer insurance documentation. Documented understanding of significant customer contractual and compliance requirements. Reduction in preventable compliance exceptions, claims, and operational risk. Successful regulatory, insurance, and customer audits. Clear, current, and consistently followed safety and compliance SOPs. Effective communication of material risks and compliance issues to Executive Leadership. QUALIFICATIONS & EXPERIENCE 5+ years of transportation safety, DOT compliance, transportation risk, carrier compliance, or related experience required. Strong working knowledge of DOT and FMCSA regulations required. Experience working within an asset based motor carrier environment required. Experience within freight brokerage, 3PL, or carrier compliance strongly preferred. Experience with Driver Qualification Files, FMCSA Clearinghouse, Hours of Service, ELD requirements, drug and alcohol testing programs, and CSA/SMS. Experience with carrier onboarding, qualification, insurance verification, and ongoing monitoring preferred. Experience working with commercial transportation insurance, claims, insurance brokers, or customer insurance requirements strongly preferred. Experience reviewing transportation customer contracts and identifying operational or insurance requirements preferred. Strong understanding of transportation operations and the ability to translate regulatory and contractual requirements into practical operating procedures. Strong organizational skills and attention to detail. Strong written and verbal communication skills. Ability to work effectively across Operations, Sales, Carrier Sales, Fleet Operations, Human Resources, Accounting, and Executive Leadership. Ability to exercise sound judgment, identify risk, and appropriately escalate significant issues. EDUCATION Bachelor’s degree in Business Administration, Transportation, Logistics, Supply Chain Management, Risk Management, Safety, or a related field preferred. Equivalent combination of relevant education and progressive transportation industry experience will be considered. Relevant professional certifications in transportation safety, DOT compliance, risk management, or insurance are a plus, including Certified Director of Safety (CDS), NATMI certifications, or similar credentials.