Director/Vice President of Sales

Roadrunner•Downers Grove, IL

5d•$170,000 - $300,000•Hybrid

About The Position

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.

Requirements

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.

Responsibilities

Lead one of Roadrunner’s strategic sales channels.
Partner closely with operations and executive teams to help shape how freight sales should operate in a category-leading company.
Build and develop top talent within sales teams.
Drive accountability, execution, and growth in fast-moving, high-pressure environments.
Leverage CRM, Power BI, and performance data to turn strategy, pipeline intelligence, and market opportunities into measurable results.