Director/Vice President of Sales

Roadrunner Transportation Systems Inc.

Downers Grove, IL

JOB DETAILS
SALARY
$170,000–$300,000 Per Year
SKILLS
Analysis Skills, Artificial Intelligence (AI), Brokerage, Cargo/Freight, Category Development, Customer Experience, Customer Relationship Management (CRM), Leadership, Less Than Truckload (LTL), Life Insurance, Logistics, Machine Learning, Network Routing, Operational Audit, Partner Sales, Power BI, Predictive Modeling, Rail Cargo, Recruiting/Staffing Agency, Risk Management, Sales, Sales Strategy, Supply Chain, Team Lead/Manager, Time Tracking, Truck Driver, Vehicle Driving, Willing to Travel
LOCATION
Downers Grove, IL
POSTED
28 days ago

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 compensation

  • Performance-based incentive opportunities

  • Hybrid / Onsite

  • Extensive travel required (50-100%)

  • Full benefits package including:

  • Medical

  • Dental

  • Vision

  • Life Insurance

  • PTO

  • Paid Holidays

  • 401(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, IL

About the Company

R

Roadrunner Transportation Systems Inc.

When it comes to finding a highly successful career path with a national industry leader, Roadrunner Transportation Systems is in it for the long haul! Our people-focused philosophy supports service excellence and fuels innovation – for our associates and clients alike. Serving more than 35,000 customers across North America with top-of-the-line transportation services made available through a network of skilled, enthusiastic professionals with a passion for getting the job done right, on time, every time. As our company continues to grow, so does our need for top talent as we expand our professional family nationwide. As a leading provider of supply chain and logistics solutions for customers with truckload transportation service needs from coast to coast, Roadrunner Transportation Systems operates a tremendous corporate network. Our scalable solutions allow us to serve a wide variety of customers in numerous markets and industries nationwide. An equal opportunity employer that supports a diverse, drug-free workplace environment, Roadrunner Transportation Systems is a company that treats its associates with the utmost respect and integrity. We are pleased to offer competitive compensation, on-the-job education and training, and numerous opportunities for advancement.

COMPANY SIZE
1,500 to 1,999 employees
INDUSTRY
Transportation and Warehousing
FOUNDED
1984
WEBSITE
https://www.rrts.com/Pages/Home.aspx