Enterprise Account Executive, Major Accounts - Midwest

cars; United States; Hybrid; USD 100,000 - 180,000; Full time

Job summary

Cars Commerce in Chicago (Midwest US) seeks an experienced Enterprise Account Executive to drive revenue across Marketplace, Accu‑Trade, and DI platforms. You will identify opportunities, manage key accounts, and close deals with a mix of remote and in-person engagements.

The role requires 5+ years in digital advertising or SaaS, strong presentation skills, and a proven track record of quota attainment. You will collaborate with multiple teams to craft tailored solutions and maximize ROI for

Qualifications

• Proven experience in planning and solution selling within complex sales cycles.

Responsibilities

• Identify and close new opportunities across assigned accounts and platforms.
• Serve as liaison for prospects and existing customers to drive growth.
• Collaborate with internal teams to support client needs and upsell.
• Coordinate with product specialists to deliver insights and strategies.
• Deliver sales presentations and demos highlighting ROI and value.
• Maintain relationships with accounts through remote and in-person interactions.

Skills

Solution selling

Collaboration

Influence & guidance

Remote work

Sales presentations

Negotiation

Digital marketplace experience

Education

Bachelor's degree or equivalent

Tools

Salesforce

HubSpot

Microsoft Dynamics

Job description

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, Cars.com, our industry‑leading digital experience, Dealer Inspire, our trade and appraisal technology, AccuTrade, our reputation‑based digital wholesale auction marketplace, Dealerclub, 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.

About the Role:

The Enterprise Account Executive (EAE) is responsible for driving revenue growth for Cars Commerce by identifying, creating, and closing opportunities within their assigned accounts. The EAE will manage and grow relationships across multiple Cars Commerce platforms, including Marketplace, Accu‑Trade, Media Solutions, and Dealer Inspire (DI) Solutions. Working closely with supporting teams, the EAE will execute on revenue growth strategies, ensuring customer success and long‑term retention. This role involves selling products and services to both new and existing customers while maintaining a focus on upselling and expanding relationships. The EAE will collaborate with the Account Executive, Major Accounts & Performance Manager (PFM) teams as well as with Product Specialists to ensure clients receive optimized, tailored solutions. This role will support accounts primarily in the Midwest US.

What You’ll Do:

• Drive revenue growth by identifying and closing new opportunities across assigned accounts and platforms.
• Act as a liaison for prospects and existing customers, ensuring customer satisfaction and growth.
• Partner with the Account Executive, Major Accounts and other internal teams to support client needs and execute on account strategy.
• Collaborate with Business Development (BD) and Customer Success teams to determine client needs and provide recommendations for upselling.
• Coordinate with Product Specialists (Marketplace, Website Solutions, Media, and Accu‑Trade) to execute sales strategies and deliver key insights through reports and analysis.
• Conduct in‑depth sales presentations, including product demos that highlight key benefits, return on investment, and the overall value of our services.
• Maintain and grow relationships with accounts through a mix of remote and in‑person interactions.

About You:

• Proven experience in planning and solution selling, with the ability to manage complex sales processes.
• Strong collaboration skills and ability to work within a team‑based environment (Pod structure).
• Ability to influence and guide team members toward common goals and objectives.
• Self‑motivated and comfortable working in a remote setting from a home office and while on the road.
• Demonstrated expertise in conducting effective sales presentations and product demonstrations that showcase our solutions' ROI and benefits.
• Strong persuasion and negotiation skills, with a focus on driving results.
• 5+ years of experience in the digital marketplace is highly preferred.
• Excellent communication, presentation, and relationship‑building skills.
• Strong business acumen with the ability to understand client needs and industry trends.
• Experience working with Business Development teams to expand reach with Accu‑Trade, Cars Commerce Media, DI Tech Solutions, and Marketplace offerings.

What You Bring:

• Proven ability to identify and close sales opportunities.
• 5-10+ years of relevant sales experience in a complex, SaaS or advertising environment.
• Bachelor’s degree or equivalent experience.
• Consistent track record of quota attainment and a drive to continuously succeed.
• CRM fluency: Salesforce (preferred), HubSpot, or Microsoft Dynamics
• Experience selling complex digital advertising, ad tech, marketing SaaS, classifieds, automotive