Expansion Drayage Director

A growing drayage and intermodal services provider is hiring an Expansion Drayage Director to own the playbook for entering new markets across the United States. This is a senior, remote, revenue-driving role built for a seasoned drayage operator who has opened new geographies before — someone who knows how to move from zero presence to a profitable book of business in a market, and who can do it again. RESPONSIBILITIES - Own the expansion strategy: identify, prioritize, and sequence new U.S. drayage markets based on port flows, rail ramp access, customer demand, and competitive landscape - Build and execute the go-to-market plan for each new territory — including early-customer acquisition, pricing strategy, local carrier relationships, and operational readiness - Lead business-development efforts personally in the first wave of expansion markets; hire and mentor sales talent as the territory scales - Partner directly with operations, dispatch, and rail/steamship partners to ensure new markets launch with service quality that protects the brand - Negotiate master service agreements and long-term contracts with national importers, exporters, 3PLs, and beneficial cargo owners - Serve as the face of the company in new markets — attend port events, trade shows, BCO meetings, and industry conferences - Deliver clear market intelligence and P&L-level reporting to executive leadership on the performance of each expansion market - Collaborate with finance and ops on rate cards, margin targets, and capital allocation for each new territory QUALIFICATIONS - 7+ years of progressive experience in drayage, intermodal, or container logistics sales, with at least 2+ years in a leadership or senior-BD capacity - Proven track record of opening new geographic markets or business units in drayage / intermodal and growing them to scale - Deep relationships at U.S. ports, rail ramps, and with national BCOs and 3PLs - Commercial instinct on pricing, margin, and contract structure in asset-based drayage - Ability to operate as a player-coach — willing to carry the first deals personally and build out the team as the market matures - Strong executive presence and ability to represent the company at the C-suite level with customers and partners - Comfort with TMS platforms, CRM discipline, and data-driven territory management - Willingness to travel heavily (30-50%) in the early ramp of each market COMPENSATION - Competitive base salary + commission/bonus tied to territory P&L - Total on-target earnings $80,000 to $150,000+ with upside as expansion markets scale - Full remote flexibility with travel to target markets and company HQ as needed - True ground-floor opportunity to build a national drayage presence — with the platform, fleet, and rail/steamship relationships already in place