Senior Director of Transportation

Opportunities to Shine and Grow.
More than a role
- RBW is where you can build a meaningful career. Whether you’re early in your journey or a seasoned professional, you’ll have opportunities to develop your skills, take on meaningful challenges, and make a difference alongside people who care deeply about the work and each other. Here, your ideas matter, your contributions are recognized, you’re part of a team, and your growth is supported
- as we elevate work and enrich lives.
Position SummaryThe Senior Director of Transportation owns the performance, capacity, and compliance of RBW Logistics' entire transportation network — freight brokerage, the Owner-Operator fleet, and the company-owned truck fleet. This role is accountable for ensuring the network has the capacity to serve customer freight profitably every day, that every driver and carrier in the network is safe and compliant, and that dispatch operations run with the discipline and visibility needed to hit service and cost KPIs. The Senior Director of Transportation partners closely with Sales, Customer Success, and executive leadership to align transportation capacity with growth commitments across RBW's markets.

Key Responsibilities
Freight Brokerage Capacity ManagementOwn end-to-end capacity planning for the brokerage division, ensuring sufficient carrier and lane coverage to meet customer commitments across all markets.
Direct the brokerage desk staff on carrier sourcing, rate negotiation, and lane strategy for both shipper-side and carrier-side operations.
Monitor freight market conditions and adjust sourcing strategy to protect margin while maintaining service levels.
Build and maintain a qualified carrier network sufficient to cover surge volume, seasonal peaks, and new account onboarding.
Partner with Sales on new business and RFQ responses to validate that committed capacity is achievable before contracts are signed.
Owner-Operator Fleet Recruitment & ComplianceLead recruitment, onboarding, and retention strategy for the Owner-Operator fleet to maintain target headcount across all operating markets.
Own the compliance vetting process for all Owner-Operators, using Highway and FMCSA SAFER as dual-verification platforms and Sunnybrook TMS as the system of record for all compliance documentation.
Ensure all Owner-Operator files (insurance, authority, safety ratings, driver qualification files) always remain current and audit-ready.
Establish and enforce minimum safety and performance standards for Owner-Operator onboarding and continued network participation.
Track Owner-Operator turnover and utilization and drive corrective action plans where attrition or non-compliance put capacity at risk.
Company-Owned Fleet OperationsOversee daily operation, utilization, and maintenance coordination of the company-owned truck fleet.
Manage Transportation Managers (East and West) to ensure driver scheduling, equipment readiness, and route assignments support daily volume requirements.
Monitor fleet cost drivers (fuel, maintenance, purchased transportation) and lead corrective action on markets running over budget.
Ensure DOT compliance, driver qualification files, and safety programs for all company drivers are current and audit ready.
Daily Dispatch Operations & KPI ManagementDirectly oversee daily dispatching across all markets, ensuring loads are covered, tendered, and tracked in Sunnybrook TMS in real time.
Set and manage the daily dispatch cadence for Carrier Dispatchers and Trans Dispatchers, resolving service exceptions as they arise.
Own the transportation KPI scorecard — on-time pickup/delivery, load acceptance/tender rejection, cost per mile, carrier/driver utilization, claims and safety incidents — and report performance to the CGO and executive leadership on a regular cadence.
Identify root causes behind KPI misses and drive corrective action plans with Transportation Managers, Brokerage, and Billing/Compliance staff.
Maintain accurate, real-time visibility into load status, capacity, and exceptions for internal stakeholders and key customer accounts.
Leadership & Cross-Functional PartnershipLead, coach, and develop the transportation and brokerage team, including the Director of Brokerage, Transportation Managers, Billing/Compliance Admin, and Dispatch staff.
Partner with Customer Success on account-level service issues tied to capacity, dispatch, or carrier performance.
Represent transportation capacity and compliance considerations in customer and executive presentations as needed.
Support budget planning and headcount requests for the transportation and brokerage organization.
This description reflects the general nature and level of work performed and is not intended to be an exhaustive list of all duties, responsibilities, and qualifications. RBW reserves the right to add, remove, or modify duties as business needs require, with or without notice.
Additional Responsibilities (Non-Essential)None identified for this role at this time.
What You'll Bri