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

About This Opportunity

Our talent team is representing a confidential trucking organization operating a 600-truck asset base. They are building their direct enterprise freight sales function from the ground up and need a strategic sales leader to drive contract pipeline development.

This is a remote role with an initial market focus on Joliet, IL and long-haul freight originating from that region. You will not be managing an existing book of business—you will be creating new enterprise relationships and getting our client's fleet in front of high-volume shippers, into their RFPs, mini-bids, and contract freight programs.

Responsibilities

• Identify and map enterprise shippers with significant freight volume in the Joliet market and surrounding regions
• Build relationships with transportation procurement, logistics, and supply chain decision-makers at target accounts
• Identify and pursue upcoming RFPs, mini-bids, pilots, and contract truckload opportunities
• Navigate carrier onboarding and qualification processes with enterprise shippers and large brokers
• Position the client's 600-truck asset base for high-volume freight opportunities
• Build and manage a qualified pipeline with clear next steps, stakeholders, timelines, and freight volume projections
• Collaborate with operations and pricing teams to convert opportunities into actionable lanes and contract awards
• Develop direct-shipper relationships that grow into recurring contract freight programs

30-Day Trial Targets: This position includes a 30-day trial period with outcome-based performance expectations, including mapping 40+ enterprise shippers, initiating 10+ procurement conversations, creating 6+ qualified opportunities with concrete next steps, starting 3+ vendor onboarding processes, securing inclusion in 3+ RFPs or pilots, receiving 2+ live bid opportunities, pricing 200+ lanes, and achieving 1 pilot or lane award representing $10M+ in annualized accessible freight.

What We're Looking For

• Proven experience in enterprise freight sales, transportation procurement, contract truckload, brokerage, 3PL, or strategic account management
• Strong understanding of how enterprise transportation procurement functions and decision-making processes
• Demonstrated ability to reach and influence senior logistics and procurement decision-makers
• Experience with shipper RFPs, mini-bids, carrier onboarding processes, or contract freight negotiations
• Track record of building a sales pipeline from scratch rather than managing inherited accounts
• Strong commercial judgment and ability to qualify opportunities based on freight volume and strategic fit
• Proficiency with data analysis, transportation technology platforms, CRM systems, and digital freight tools
• Highly proactive, self-directed work style with comfort being measured by concrete outcomes

How We Work With You

Candidates apply directly through Get A Job.ai. Our recruiting team will conduct an initial screening to understand your background and match with the role. Qualified candidates are then submitted to our client for consideration. Please do not attempt to contact the client directly, as all communication is managed through our team to ensure a professional and coordinated process.

Pay

Compensation details will be discussed during the screening process based on experience and qualifications.

Equal Opportunity: Get A Job.ai is committed to inclusive recruiting practices. We welcome applications from candidates of all backgrounds and work to ensure fair consideration throughout the hiring process.