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 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)

* We will not accept unsolicited candidates from external recruiters or recruiting agencies. Thank you!

#LI-Hybrid

About Roadrunner

Roadrunner is for ambitious, smart people who excel at execution over talking about it, and who would rather invent the next standard in freight than accept the status quo.

We are looking for the Best of the Best. Action driven leaders who want to be part of real change and help design the future of LTL in the U.S. This is a place where high performers can grow, influence outcomes, and make an impact while working directly with executives and smart people from across industries.

We bring a winner mindset. We take ownership, raise the bar, and measure ourselves by results. We Run Safe. We Run Smart. We Run Together. These principles create an environment of high standards, clear ownership, and direct collaboration. We trust data over intuition, move with urgency, and hold each other accountable because winning requires it.

Roadrunner exists to prove that LTL can be better than the industry has settled for. To be the best means we need to think bigger, look outside the box, and question every assumption: too many handoffs, limited visibility, and the quiet belief that “this is just how it works.” We rejected that story. We built a proprietary Smart Network™ for direct, long haul, metro to metro service that delivers fewer touches, faster transit, real time visibility, and genuine accountability. We are the most tech forward company in LTL, and we are not finished widening the gap.

The foundation is already strong. Recognized as one of Built In Chicago’s Best Large Places to Work. Earning top marks for improvement, quality, and service. The real opportunity is still ahead: helping invent what comes next.

If you want to be evaluated among the Best of the Best and help set the new standard in LTL, we should talk.