Director/Vice President of Sales

Help Build the Future Category Leader of Less-Than-Truckload (LTL) Unlike any other LTL transportation company, we’re building one of the smartest tech forward long haul networks in North America, powered by direct metro to metro routing, AI driven visibility, self-service technology, operational performance, and a wining driven mindset. And we’re growing fast. This role is for a sales leader who gets excited about building teams of sales athletes.Are you someone who knows how to build ultra-high-performance sales teams with a unique competitive edge? Can you bring energy, accountability, analytical thinking, and execution discipline into a rapidly scaling organization? If yes, you could be a fit. Someone who: Loves building competitive, high-performance cultures and developing top talent Knows how to lead through pressure, accountability, and ambitious growth expectations Uses data, CRM insights, Power BI, and execution discipline to outperform the market Understands that winning in transportation requires operational alignment, not just selling Thrives in fast-moving, high-expectation environments where standards are high and comfort zones are low Raises the intensity of the people around them and pushes teams toward stretch performance. This role combines commercial leadership, operational thinking, analytics, and people selection, talent bench and performance. You’ll lead one of Roadrunner’s strategic sales channels while partnering closely with operations and executive teams to help shape how freight sales should operate in a category-leading company. The people who thrive here are builders. People who want ownership. People who want to help create something category-defining inside an industry ready for change. What you bring 10+ years of sales leadership experience in transportation, logistics, LTL, brokerage, or supply chain, with proven success building high-performance teams Competitive mindset with the ability to drive accountability, execution, and growth in fast-moving, high-pressure environments Strong commercial, operational, and analytical leadership skills with a sales-engineer mindset — capable of leveraging CRM, Power BI, and performance data to turn strategy, pipeline intelligence, and market opportunities into measurable results Compensation & Setup $170–$300k total compensationPerformance-based incentive opportunitiesHybrid / OnsiteExtensive travel required (50–100%)Full benefits package including: MedicalDentalVisionLife InsurancePTOPaid Holidays401(k)About Roadrunner We’re completely reinventing long-haul Less-Than-Truckload (LTL) shipping. Our Smart Network offers more direct long-haul metro-to-metro routes than any other nationwide LTL carrier in the United States, with service extending into Canada and Mexico and service centers across 40+ metro markets. Powered by AI and machine learning, our operations platform ensures real-time tracking, custodial control, and full shipment visibility. With driver teams executing over-the-road (OTR) moves, and no freight moving on rail, customers experience industry-leading transit times, minimal rehandling, and dramatically reduced risk of loss or damage. Our 1,000+ owner-operators benefit from scheduled freight, fewer touches by design, consistent long-haul density, and a differentiated metro-to-metro model that creates predictable earning opportunities. This precision and performance have earned Roadrunner national recognition by over 3,000 shippers, and was ranked this year #1 in Operations, #1 in Technology, and #1 in Value in the Quest for Quality Awards, as well as honors as a Top 100 Trucking Company by Inbound Logistics and a Top Tier Service Carrier by Mastio. We’re growing fast. Roadrunner is building something special with great people, a winning culture and a differentiated service offering in the marketplace. Join us today to grow your career! Our Guiding Principles: We Run Safe. We Run Smart. We Run Together. * We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!#LI-OnsiteDowners Grove, IL#LI-HybridDowners Grove, ILSummaryLocation: Downers Grove ILType: Full time