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

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