Driver Manager, Owner-Operator

Job Summary PortCity Logistics is seeking an experienced, results-driven Owner-Operator Manager to oversee, scale, and optimize our independent contractor fleet. Currently managing roughly 50 owner-operators with aggressive plans for material fleet growth over the next few years, this leader will serve as the primary relationship owner and operational anchor for our contractor network. The ideal candidate brings deep expertise in motor carrier compliance, settlement administration, commercial dispute resolution, and driver recruitment. You will balance rigorous compliance and accountability with driver advocacy to establish PortCity Logistics as the carrier of choice for premier owner-operators and lease drivers. Ideal Candidate: 5–7 years of relevant trucking or transportation experience. Demonstrated success managing owner-operators or independent contractors. Strong interpersonal skills, conflict resolution, and relationship management. Experience recruiting and retaining quality owner-operators. Working knowledge of DOT/FMCSA requirements and contractor settlements. Experience in drayage, intermodal, or combined local/OTR operations is preferred. Contractor Relationship Management & Retention Serve as the primary point of contact for all contracted owner-operators, building strong, collaborative working relationships that drive high retention and loyalty. Act as an advocate for fleet partners while ensuring alignment with PortCity Logistics' operational goals, service standards, and safety culture. Implement structured feedback channels and regular engagement touchpoints to identify operational friction points and improve day-to-day driver satisfaction. Settlement Administration & Financial Operations Oversee transparent, accurate, and timely weekly settlement processing, deductions, fuel surcharges, and accessorial pay reconciliations. Partner with accounting and finance teams to audit settlement statements, resolve discrepancies promptly, and maintain clear financial records for every contractor. Provide clear guidance to drivers regarding settlement structures, profitability metrics, and revenue optimization opportunities. DOT & Safety Compliance Maintain strict adherence to Federal Motor Carrier Safety Administration (FMCSA) regulations and Department of Transportation (DOT) compliance standards across the entire contractor fleet. Manage qualification files, annual reviews, clearinghouse queries, drug and alcohol testing compliance, hours-of-service (HOS) monitoring, and equipment safety inspections. Enforce company safety protocols swiftly and fairly, mitigating risk and protecting the operating authority of PortCity Logistics. Commercial Disagreements & Dispute Resolution Act as an objective, decisive mediator for all commercial, operational, and financial disagreements between contractors and internal dispatch or logistics teams. Develop and enforce clear standard operating procedures (SOPs) for handling claims, chargebacks, detention disputes, and contract terminations. Protect company interests while maintaining professional, fair, and legally sound resolutions to complex disputes. Recruitment & Fleet Expansion Strategy Drive end-to-end recruitment strategies to aggressively scale the owner-operator fleet over the coming years, utilizing targeted marketing, referral programs, and industry networking. Design and execute competitive compensation packages, lease-purchase terms (if applicable), and onboarding pipelines to attract high-caliber independent talent. Conduct rigorous vetting, qualification, and orientation processes to ensure incoming contractors meet PortCity Logistics' strict cultural, safety, and performance standards. Qualifications & Requirements Experience: Minimum of 5–7 years of progressive experience in transportation operations, specifically managing independent contractor, owner-operator, or fleet management programs within the logistics or trucking industry. Regulatory Expertise: Co…

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