Senior Sr. Account Executive - Central & Western Massachusetts

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.

Candidates must reside within the assigned territory (anchored by Worcester, Springfield, Gardner/Fitchburg, and Greater Boston’s Metro West) and be able to travel by car for face-to-face visits with existing and prospective customers.

About the Role

Act as the primary point of contact for Cars Commerce customers, focusing on ongoing customer success, retention, and growth.

Sell products and services to existing customers. Maintain relationships through regular in-person visits within an assigned geographic territory. Respond to client inquiries and recommend appropriate products and services.

Execute sales strategy, identify and close upsell opportunities. Prepare reports and deliver insights that communicate measurable value to customers. Demonstrate expertise in Cars Commerce products, services, and the digital automotive marketplace.

Manage pipeline with discipline — maintain daily Salesforce hygiene, track pipeline coverage ratios, forecast accurately, and apply a structured sales methodology at every stage.

Travel (primarily driving but occasional flights) at least 75% of the time within the assigned territory for face-to-face customer engagement.

Partner across selling and servicing roles at Cars Commerce to ensure customers receive maximum value from the Cars Commerce Platform.

What We're Looking For: The DRIVE Profile

Every successful Cars Commerce AE embodies all five dimensions of DRIVE:

COMPETENCY

WHAT IT MEANS

D

Disciplined

Pipeline rigor, Salesforce hygiene, forecasting accuracy, and use of structured sales methodology

R

Results-Proven

Consistent, multi-year quota attainment — backed by specific numbers, deal sizes, and rankings

I

Interconnected Solution Seller

Media/digital advertising or SaaS background; comfortable owning SMB and mid-market accounts

V

Voraciously Hungry

Grit, tenacity, and fire — personal ownership of outcomes, self-driven activity beyond what's required

E

Earning-Motivated

Financial drive is the engine — unapologetically money-motivated with a preference for uncapped commission

Qualifications

• Excellent planning and solutions-selling experience with a structured, repeatable methodology — Sandler, Challenger, SPIN, or Consultative Selling.
• Motivated and comfortable working remotely from a home office as well as from the road and field.
• Ability to conduct in-depth sales presentations including product demonstrations that highlight key benefits, ROI, and the value of our solutions.
• Proven persuasion and negotiation skills, with the tenacity to re-engage stalled deals and push through friction.
• Experience in the automotive space or digital marketplace strongly preferred.
• Excellent communication, presentation, and customer relationship-building skills.
• Strong business acumen — knows their pipeline coverage ratio, conversion rates by stage, and forecast accuracy.

Requirements

• 5–10 years of progressive B2B sales experience with a media, digital advertising, marketing SaaS, or automotive solutions background.
• Proven, multi-year quota attainment record — candidates must be prepared to share specific quota figures, attainment percentages, and team/regional rankings.
• Demonstrated Salesforce proficiency with strong CRM hygiene habits; daily updates and pipeline reviews are the norm, not the exception.
• Demonstrated track record of consistent quota attainment and a continuous, competitive drive to win.
• Experience selling advertising or complex SaaS/software solutions to business leaders in SMB or mid-market segments.
• Bachelor's degree or equivalent experience.
• Financially motivated with a preference for uncapped, accelerated commission structures over high-base/low-variable plans.

Compensation

In the spirit of pay transparency, we are excited to share the compensation for this role. The range is expressed as total target compensation (base salary + variable). Actual compensation is determined based on skills and/or experience.

In this spirit of pay transparency, we are excited to share the compensation for this role. The range is expressed as total target compensation (base salary + variable). If you are hired at Cars Commerce, your total target compensation will be determined based on factors such as skills and/or experience. If the range is close to what you're seeking, then we encourage you to apply and learn more about the total compensation package and benefits for this position. Total Target Compensation Range $154,200.00-192,750.00

Our Comprehensive Benefits Package includes:

• Medical, Dental & Vision Healthcare Plans
• New Hire Stipend for Home Office Set-Up
• Generous PTO
• Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day

Learn more about our Benefits, Perks, & Culture on our LinkedIn Life Pages!

For US-based Positions: Applicants must be authorized to work in the United States. Please note that we are unable to sponsor employment visas at this time.
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