Director, Field Sales - MidSouth

Be Essential At Cars Commerce

At Cars Commerce, we’re fanatical about simplifying everything about car buying and selling. We do right by our customers and consumers to better connect the industry with simplified and tierless technology to enhance, measure and drive local automotive retail. Whether through our No.1 most recognized marketplace, , our industry-leading digital experience, Dealer Inspire, our trade and appraisal technology, Accu Trade, our reputation-based digital wholesale auction marketplace, Dealer club, or our new Cars Commerce Media Network, Cars Commerce is essential for success in the automotive industry.

No one ever travels alone here: at its core, Cars Commerce is collaboration. In fact, it’s built into the very fabric of our shared values. We like to say we Rise Together – putting people at the center of what we do, from consumer to customer to community. Life at Cars Commerce makes it easy when we share the ethos to be Open to All, encouraging open-minded communication because we know diverse thinking yields better outcomes.

But critical to our success is Caring to Challenge and Taking Ownership, fueling a competitive spirit in a respectful environment where we think about tomorrow but act today. At our foundation, we have integrity, Doing the Right Thing, even when it’s hard. It’s our shared commitment to these values that makes Cars Commerce a place where growth becomes not only possible, but downright unavoidable.

But don't take our word for it. We are proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S. Ready to make your mark? Join a team that's driving real change in the automotive industry.

The Group Director is a senior field sales leader responsible for driving revenue growth and commercial excellence across a multi-territory region. In this role, you will lead a team of approximately 15 Senior Account Executives — seasoned, consultative sellers operating across geographically distributed dealer territories — and serve as the connective tissue between front-line field execution and the strategic direction set by the Field VP.

Senior Account Executives, Account Executives, Account Managers, and Client Partners (media and website sales specialists) all report up through this role. The Group Director is accountable not just for the output of the team, but for the standard of talent, culture, and execution that defines it.

This is a player-coach leadership role for someone who thrives in a high-complexity, high-accountability environment. You know how to develop elite sellers, manage a large and dynamic pipeline, and build the kind of team culture that wins consistently. You bring deep automotive or vertical SaaS experience, strong executive presence, and the operational rigor to run a scaled field organization without losing sight of the individual dealer relationships that drive growth.

• Lead, coach, and develop a team of ~15 Senior Account Executives across a defined multi-state region
• Conduct regular field rides, deal reviews, and one-on-ones to assess performance, reinforce consultative selling behaviors, and accelerate skill development
• Partner with HR and Talent Acquisition to recruit, onboard, and retain top-tier field sales talent — screening for the full DRIVE profile at every hire
• Build a high-performance team culture grounded in accountability, intellectual curiosity, financial hunger, and dealer-first thinking
• Identify and develop future leaders within the team; model the behaviors you want replicated at every level below you

• Own regional revenue targets across the full Cars Commerce portfolio:  marketplace, Dealer Inspire, Accu-Trade, and digital media solutions
• Maintain rigorous regional pipeline and forecasting discipline in Salesforce; roll up a reliable, evidence-based forecast to the Field VP on a weekly and monthly cadence
• Drive consistent attainment across the entire team — not just top performers — through structured coaching and performance management
• Identify revenue risk early and implement proactive mitigation…