Senior Director, Land Transportation and Brokerage Operations

Senior Director, Land Transportation and Brokerage Operations - Build a Scalable Transportation Network & Drive Growth

The Pasha Group is seeking a strategic transportation leader to drive the growth, profitability, and operational excellence of its Land Transportation and Brokerage operations. As Senior Director, you will lead purchased transportation, freight brokerage, dispatch, intermodal, and carrier network strategies supporting Household Goods, Commercial, and Hawaii trade lane customers.

This is a high-impact leadership opportunity to build and scale a growing brokerage business, strengthen carrier partnerships, optimize transportation solutions, and develop high-performing teams across geographically dispersed operations. You'll work closely with Sales, Customer Service, Operations, and executive leadership to expand capabilities, improve service, and deliver sustainable financial results.

Build & Scale Freight Brokerage Operations

Lead the strategy, infrastructure, and growth initiatives that establish a scalable and profitable brokerage business.

• Lead Brokerage Strategy: Develop and execute enterprise-wide strategies for purchased transportation, freight brokerage, dispatch, and carrier network operations.
• Build the Business: Lead the startup, development, and expansion of brokerage operations, including organizational design, operating models, technology, carrier acquisition, and customer growth.
• Expand Market Opportunities: Develop transportation solutions that grow market share, strengthen customer relationships, and create new revenue opportunities.
• Optimize Brokerage Performance: Develop strategies that maximize brokerage margins, control freight costs, and maintain agreed service levels.
• Leverage Technology: Drive implementation and optimization of brokerage platforms, load boards, dispatch systems, TMS solutions, and analytics tools.

Lead Transportation, Dispatch & Carrier Operations

Ensure reliable capacity, efficient execution, regulatory compliance, and exceptional service across a complex transportation network.

• Direct Transportation Operations: Oversee OTR, local trucking, drayage, Full Container Load (FCL), rail, intermodal, and third-party carrier solutions.
• Optimize Capacity & Routing: Lead strategies for routing, scheduling, capacity utilization, service performance, and cost effectiveness.
• Strengthen Carrier Networks: Direct carrier sourcing, vetting, onboarding, compliance, performance management, and relationship development.
• Manage Strategic Partnerships: Negotiate transportation contracts, service agreements, rates, and strategic carrier partnerships aligned with business objectives.
• Drive Compliance & Risk Management: Ensure adherence to transportation regulations, safety requirements, track-and-trace standards, operating procedures, and risk management practices.
• Improve Visibility: Establish customer communication and shipment visibility standards that support proactive issue resolution and reliable service.

Drive Financial Performance & Operational Excellence

Turn transportation data, market intelligence, and financial insight into stronger performance and sustainable growth.

• Manage Financial Performance: Lead planning, budgeting, forecasting, cost control, and profitability management for transportation and brokerage operations.
• Optimize Costs: Identify opportunities to reduce transportation costs while protecting service quality and maximizing margins.
• Monitor Performance: Establish KPIs, reporting processes, and performance standards to measure operational effectiveness, carrier performance, customer satisfaction, and brokerage growth.
• Resolve Financial Issues: Oversee carrier and vendor billing disputes, invoice issues, contract compliance, and rate negotiations.
• Use Data to Drive Decisions: Leverage technology, analytics, and market intelligence to identify trends, solve complex challenges, and continuously improve operations.
• Report to Leadership: Communicate operational performance, growth initiatives, financial results, and strategic priorities to executive leadership.

Build High-Performing Teams & Strategic Partnerships

Develop strong leaders, create accountability, and build collaborative relationships across the organization and transportation industry.

• Lead Distributed Teams: Manage and develop geographically dispersed leadership teams and multi-site operations.
• Develop Leadership Talent: Build organizational capability, succession strength, and a strong pipeline of future leaders.
• Set Clear Expectations: Establish performance standards, accountability measures, and continuous improvement initiatives across transportation and brokerage operations.
• Partner Across the Business: Collaborate with Sales, Customer Service, Operations, and other leaders to create transportation solutions that meet customer needs.
• Strengthen Industry Relationships: Build trusted relationships with carriers, vendors, customers, and industry partners.
• Inspire Performance: Lead with energy, accountability, and a customer-focused mindset that motivates teams to achieve ambitious goals.

What You Bring

• Education: Bachelor's degree in Logistics, Supply Chain Management, Business Administration, or a related field, or an equivalent combination of education and experience required.
• Experience: 10+ years of transportation, logistics, purchased transportation, freight brokerage, and/or dispatch leadership experience.
• Leadership: 6+ years managing transportation, brokerage, or logistics operations and budgets.
• Brokerage Expertise: Proven experience building, launching, and scaling freight brokerage operations.
• Carrier Network Experience: Experience managing owner-operator networks, carrier partnerships, and contract service delivery models.
• Multi-Site Leadership: Demonstrated success leading geographically dispersed teams and multi-site operations.
• Financial Acumen: Strong experience with budgeting, forecasting, profitability management, and operational financial performance.
• Technology: Proficiency with TMS, brokerage platforms, dispatch software, data analytics tools, and Microsoft Office; Trinium and Truckmate TMS experience preferred.
• Industry Knowledge: Advanced knowledge of transportation, freight brokerage, carrier management, intermodal rail operations, compliance, pricing, and margin optimization.
• Communication: Exceptional verbal, written, presentation, negotiation, and relationship-building skills.
• Certification: Certified Transportation Professional (CTP) or Certified in Transportation and Logistics (CTL) preferred.

Why You'll Love Working at The Pasha Group

At The Pasha Group, you'll have the opportunity to shape transportation strategy, build new capabilities, and make a measurable impact on growth and profitability. We value Excellence, Honesty, Integrity, Innovation, and Teamwork and empower leaders to think strategically, develop people, and create solutions that move our business forward.

Work Environment & Travel

This position works primarily in a corporate office environment and involves regular communication, computer use, meetings, and collaboration with teams across the organization. Occasional travel is required, including the ability to travel independently to U.S. locations, including Hawaii.

Screening Requirements
Background Checks

The information included in this description has been designed to indicate the general nature and level of work performed by employees within this classification. It is not designed to contain or be interpreted as a comprehensive or exhaustive inventory of all duties, responsibilities, and qualifications required of employees assigned to this job.

The Pasha Group family of companies are EOE/AA Employers - Minority/Female/Veteran/Disabled/and other Protected Categories

Ready to Lead the Future of Transportation?

Bring your transportation expertise, entrepreneurial mindset, and strategic leadership to The Pasha Group. Apply Now and help build a scalable, high-performing transportation and brokerage network that drives customer value and long-term growth.