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
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.
Skills Required
- 10+ years of sales leadership experience in transportation, logistics, LTL, brokerage, or supply chain
- Proven success building and developing high-performance sales teams and driving accountability
- Strong commercial, operational, and analytical leadership skills with a sales-engineer mindset
- Proficiency with CRM systems and Power BI to analyze pipeline, performance data, and inform strategy
- Ability to work hybrid/onsite and travel extensively (50-100%)
- Experience partnering closely with operations and executive teams to align sales and operational execution
Roadrunner Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Roadrunner and has not been reviewed or approved by Roadrunner.
-
Retirement Support — Benefits for W‑2 staff include a 401(k), and some materials reference matching contributions for certain corporate roles. This provides a conventional savings vehicle even though current match details are not broadly published.
-
Leave & Time Off Breadth — Corporate/operations postings cite paid time off and paid holidays as part of the package. This indicates a standard time‑off framework for employees.
-
Flexible Benefits — Company and third‑party profiles mention extras such as FSAs, tuition assistance, mental‑health support, and pet insurance for some roles. These additions extend flexibility beyond core medical and retirement.
Roadrunner Insights
What We Do
Roadrunner is the Smart Choice for long-haul, metro-to-metro LTL service throughout the country. With terminals across 40+ markets and a nationwide presence, Roadrunner’s Smart Network is the best option for shippers looking to move freight quickly and reliably. The company provides high-quality, scalable LTL freight services to shippers of all sizes across various industries. Roadrunner’s Smart Long Haul is revolutionizing the Less-than-Truckload industry with investments in technology, a culture of continuous improvement, and intelligent and efficient direct routing. Every day, the team at Roadrunner challenges itself to be more innovative and creative than the day before by setting high expectations and solving problems before they even happen. Our award-winning culture gives people the autonomy to build innovative solutions while taking a data-driven approach to become the Smart Choice for LTL shippers. At Roadrunner, we run safe, we run smart, and we run together.
Why Work With Us
WE RUN SAFE -We learn, train, and share safety best practices. WE RUN SMART -We use technology to optimize our operations. -We create opportunities for ourselves, our teammates, our customers, and our business. WE RUN TOGETHER -We celebrate each other's accomplishments. -We acknowledge our wins but are not afraid to fail. We are partners.
Gallery
