Senior Director, Transportation

Job Summary

The Senior Director, Land Transportation and Brokerage Operations provides strategic and operational leadership for purchased transportation, freight brokerage, dispatch, and carrier network operations, driving the startup, growth, and profitability of brokerage services while supporting Over-the-Road (OTR), Intermodal, and third-party carrier solutions for Household Goods (HHG), Commercial, and Hawaii trade lane customers.

Primary Objectives

• Develop and execute enterprise-wide purchased transportation and freight brokerage strategies that support business growth, operational excellence, customer satisfaction, and profitability.

• Build, scale, and optimize the brokerage business through organizational development, carrier network expansion, technology implementation, process standardization, and revenue generation initiatives.

• Provide direct leadership for transportation, dispatch, intermodal, and brokerage operations to ensure service reliability, capacity availability, regulatory compliance, and cost-effective execution.

• Manage, lead, and develop geographically dispersed leadership teams while establishing performance expectations, accountability, and continuous improvement initiatives that support strategic and financial objectives.

Duties and Responsibilities

• Develop and execute strategic plans for purchased transportation, freight brokerage, dispatch, and carrier network operations.

• Lead the startup, development, and expansion of the freight brokerage business, including organizational design, operating models, technology platforms, carrier acquisition, and customer growth strategies.

• Oversee and ensure the effective management of day-to-day activities of transportation, dispatch, and brokerage teams responsible for all modes of transportation, including Full Container Load (FCL), OTR, local trucking, drayage, rail operations, and intermodal services.

• Establish and implement transportation and brokerage strategies that improve operational efficiency, increase profitability, expand market share, and reduce costs.

• Direct the development and implementation of brokerage dispatch, load board management, carrier compliance, pricing, and transportation management systems that support scalable operations.

• Establish performance standards, key performance indicators (KPIs), and reporting processes to monitor operational effectiveness, carrier performance, brokerage growth, and customer satisfaction.

• Develop and monitor compliance with track-and-trace procedures and customer communication standards to provide proactive visibility and issue resolution.

• Develop and monitor compliance with standard operating procedures, transportation regulations, safety requirements, and risk management standards.

• Direct transportation and dispatch leadership teams to optimize routing, scheduling, capacity utilization, service performance and cost effectiveness.

• Lead carrier sourcing, vetting, onboarding, compliance oversight, and relationship management activities.

• Negotiate transportation contracts, service agreements, and strategic carrier partnerships that support operational and financial objectives.

• Evaluate carrier and vendor performance and implement corrective actions and improvement initiatives as needed.

• Collaborate with Sales, Customer Service, and Operations leadership to develop transportation solutions that meet customer requirements and support business growth.

• Utilize technology, analytics, and market intelligence to drive informed decision-making and continuous operational improvement.

• Develop and implement strategies to optimize freight costs while maintaining agreed service levels and maximizing brokerage margins.

• Develop and maintain effective professional relationships with carriers, vendors, customers, and industry partners.

• Lead planning, budgeting, forecasting, and financial management activities for transportation and brokerage operations.

• Oversee the resolution of carrier and vendor billing issues, invoice disputes, contract compliance matters, and rate negotiations to support operational efficiency and financial performance.

• Communicate operational performance, growth initiatives, and financial results to executive leadership.

• Develop leadership capability, succession strength, and organizational effectiveness across geographically dispersed management teams.

QUALIFICATIONS

Education

• Bachelor’s degree in Logistics, Supply Chain Management, Business Administration, or a related field, or an equivalent combination of education and experience required

Work Experience

• 10+ years’ experience in transportation, logistics, purchased transportation, freight brokerage, and/or dispatch leadership required

• 6+ years’ managing transportation, brokerage, or logistics operations and budgets required

• Experience building, launching, and scaling freight brokerage operations required

• Experience managing owner-operator networks, carrier partnerships, and contract service delivery models required

• Experience leading geographically dispersed teams and multi-site operations required

• Experience with budget management, forecasting, and operational financial performance required

Required Knowledge, Skills, and Abilities

• Advanced knowledge of transportation, purchased transportation, dispatch, freight brokerage, and carrier management principles.

• Strong knowledge of intermodal rail operations, transportation regulations, and industry best practices.

• Thorough knowledge of freight brokerage operations, carrier sourcing, carrier vetting, compliance management, pricing strategies, and margin optimization.

• Demonstrated ability to develop and execute strategic growth plans and business expansion initiatives.

• Strong leadership skills with demonstrated ability to motivate, influence performance, and lead by example.

• Ability to establish and communicate clear operational policies, procedures, performance expectations, and accountability measures.

• Strong verbal, written, presentation, and negotiation skills.

• Strong financial acumen, including budgeting, forecasting, profitability management, and cost control.

• Ability to analyze complex operational challenges, evaluate alternatives, and implement effective solutions.

• Proficiency in transportation management systems (TMS), brokerage platforms, dispatch software, and data analytics tools.

• Proficiency with Microsoft Office Suite.

Competencies

• Builds High-Performing Teams Selects, organizes, and motivates colleagues to work together in a committed way to achieve a common mission and ensures a pipeline of talent for the future.

• Delivers Results Rigorously drives self and others to achieve high levels of individual and organization performance.

• Engages & Inspires Others Leads with energy, self-confidence and understanding in ways that motivate colleagues to achieve more than they thought possible.

• Focuses on the Customer & Market Continuously evaluates what is important to the customer/client and develops products or solutions that exceed expectations.

• Makes Sound Business Decisions Makes timely and well-informed decisions that advance critical priorities, capitalize on new opportunities, and resolve problems.

• Partners Across Boundaries Works collaboratively and effectively with colleagues throughout the company toward the common good of The Company

• Practices our Values Supports and models The Company Way; conduct reflects Excellence, Honesty, Integrity, Innovation and Teamwork.