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

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Identify and map enterprise shippers with meaningful freight volume in the Joliet market.

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Build relationships with transportation procurement, logistics, and supply chain decision-makers.

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Identify upcoming RFPs, mini-bids, pilots, and contract truckload opportunities .

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Get Spotter through shipper and enterprise-broker carrier onboarding and qualification processes .

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Position our 600-truck asset base for high-volume freight opportunities.

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Build a qualified pipeline with clear next steps, stakeholders, timelines, and freight volume.

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Work with operations and pricing to turn opportunities into actionable lanes and awards.

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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:

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40 Joliet-area enterprise shippers fully mapped

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10 conversations with transportation procurement / logistics decision-makers

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6 qualified direct-shipper opportunities with a concrete next step

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3 new vendor onboarding / provider qualification processes initiated

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3 shippers agreeing to include Spotter in an upcoming RFP, mini-bid, or pilot

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2 live direct-shipper RFP / mini-bid / pilot opportunities received

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200+ lanes of actual Joliet-origin/local freight opportunities Spotter can price

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1 pilot or lane award

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$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

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Experience in enterprise freight sales, transportation procurement, contract truckload, brokerage, 3PL, or strategic accounts

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Strong understanding of how enterprise transportation procurement works

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Proven ability to reach senior logistics and procurement decision-makers

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Experience with shipper RFPs, mini-bids, carrier onboarding, or contract freight

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Ability to build a pipeline from scratch rather than rely on an inherited book of business

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Strong commercial judgment and ability to qualify opportunities based on actual freight volume and fit

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Comfortable working with data, transportation technology, CRM systems, and digital freight platforms

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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.

Originally posted on Himalayas