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Director of Sales (Inside)

United States, Chicago, IL 150000.00 USD / Year · Job Posted January 20, 2026
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Job Description

This is a rare opportunity to build and own an inside sales function from the ground up within a well-established, profitable B2B services organization serving commercial trucking fleets. Backed by significant growth capital and recently validated through a McKinsey-led review, the business is positioned for its next phase of scalable growth – and inside sales is a critical lever.

Job Responsibility

  • Lead the design, execution, and scaling of an outbound inside sales organization focused on selling directly to trucking and fleet operators
  • Take ownership of structure, tooling, KPIs, and team development – turning an underdeveloped function into a predictable, high-performing growth engine
  • Balance strategy with execution and work closely with senior leadership to define how inside sales operates moving forward

Requirements

  • 3+ years of inside sales / call center leadership experience
  • Proven track record building, coaching, and scaling outbound sales teams
  • Experience implementing dialers, Salesforce, and KPI-driven sales environments
  • Comfortable owning both strategy and day-to-day execution
  • Bachelor’s degree preferred

Nice to have

Industry experience not required (business will teach the market)

What we offer

  • Medical, Dental, Vision
  • 401(k) with company match
  • Travel Expenses: Covered (limited travel
  • primarily office-based)
  • 20% Bonus, uncapped

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