VP of Freight Sales – FTL / Truckload | Remote or Joliet IL

Workplace: none We are looking for a modern, highly proactive enterprise freight sales leader to build our direct-shipper contract pipeline from the ground up. This is not a traditional freight sales role focused on maintaining an existing book of business. Your mission is to get Spotter's 600-truck fleet in front of high-volume enterprise shippers and into their RFPs, mini-bids, pilots, and contract freight programs. You will identify high-value shippers, reach transportation procurement and logistics decision-makers, navigate carrier onboarding and qualification processes, and turn those relationships into real freight opportunities. Initial Market Focus This role will initially focus on local work around Joliet, IL and long-haul freight originating from the Joliet area. What You'll Own Identify and map enterprise shippers with meaningful freight volume in the Joliet market. Build relationships with transportation procurement, logistics, and supply chain decision-makers. Identify upcoming RFPs, mini-bids, pilots, and contract truckload opportunities . Get Spotter through shipper and enterprise-broker carrier onboarding and qualification processes . Position our 600-truck asset base for high-volume freight opportunities. Build a qualified pipeline with clear next steps, stakeholders, timelines, and freight volume. Work with operations and pricing to turn opportunities into actionable lanes and awards. Develop direct-shipper relationships that can grow into recurring contract freight. 30-Day Trial Targets This position begins with a 30-day trial period with clear, measurable expectations. By Day 30: 40 Joliet-area enterprise shippers fully mapped 10 conversations with transportation procurement / logistics decision-makers 6 qualified direct-shipper opportunities with a concrete next step 3 new vendor onboarding / provider qualification processes initiated 3 shippers agreeing to include Spotter in an upcoming RFP, mini-bid, or pilot 2 live direct-shipper RFP / mini-bid / pilot opportunities received 200+ lanes of actual Joliet-origin/local freight opportunities Spotter can price 1 pilot or lane award $10M+ annualized direct-shipper freight represented by accessible Joliet-area opportunities These are outcome-based targets , not activity quotas. Success in this role is measured by creating real enterprise freight opportunities and moving them toward bids, pilots, and awarded lanes. What We're Looking For Experience in enterprise freight sales, transportation procurement, contract truckload, brokerage, 3PL, or strategic accounts Strong understanding of how enterprise transportation procurement works Proven ability to reach senior logistics and procurement decision-makers Experience with shipper RFPs, mini-bids, carrier onboarding, or contract freight Ability to build a pipeline from scratch rather than rely on an inherited book of business Strong commercial judgment and ability to qualify opportunities based on actual freight volume and fit Comfortable working with data, transportation technology, CRM systems, and digital freight platforms Highly proactive, self-directed, and comfortable being measured by outcomes Why Spotter Spotter operates a 600-truck asset base , giving you the capacity and operational foundation to pursue meaningful enterprise freight opportunities. Your role is to connect that capacity with the right shippers, procurement teams, and contract freight programs — and turn those opportunities into lanes, pilots, and long-term strategic accounts.