Spotter Labs

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

Remote remote Senior Salary not listed
remote Senior level Technology & IT Curated
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About the role

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.
Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Senior
Technology & IT CRM Operations Remote Collaboration Sales Senior level remote

Likely questions

  1. Tell us about work you have done that is close to the VP of Freight Sales – FTL / Truckload | Remote or Joliet IL role.
  2. How would you approach your first 30 days at Spotter Labs?
  3. Which of CRM, Operations and Remote Collaboration have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you stay organised and communicate clearly when working remotely?

Prepare before the call

  • A recent example that proves your experience with CRM, Operations and Remote Collaboration.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the VP of Freight Sales – FTL / Truckload | Remote or Joliet IL role because I can bring practical experience in CRM, Operations and Remote Collaboration, learn the team quickly, and contribute to the outcomes Spotter Labs needs from this hire.

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