Senior Account Executive - Boston, MA

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.

Territory: Boston, MA

Candidate must reside in territory.

We are building a next-generation field sales organization, and the Sr Account Executive is at the center of that vision. This is not a transactional role. It is a consultative, solutions-oriented position for a seasoned seller who can walk into a dealership’s GM or dealer principal office, quickly diagnose their business challenges, and architect a multi-product solution across our full portfolio.

This high-visibility individual contributor role has significant earning potential, direct field presence, and a clear mandate: elevate how we sell, deepen how we partner, and grow revenue across your dealer portfolio. The Sr Account Executive is a level above our Field Account Executive. Candidates must demonstrate mastery of the full DRIVE framework—not just meeting criteria, but consistently modeling each dimension at a senior level.

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

• D — Disciplined: Rigorous pipeline management, Salesforce hygiene, and forecasting accuracy—demonstrated across a large, complex territory
• R — Results-Proven: Multi-year track record of meeting or exceeding quota on complex, multi-product deals—not just strong individual years
• I — Interconnected Solution Seller: Sells across an integrated platform; connects media, digital retailing, data, and trade tools to unified dealer outcomes
• V — Voraciously Hungry: Grit and tenacity to win in a competitive market; intellectual curiosity to stay ahead of automotive retail trends
• E — Earning-Motivated: Unapologetically money-motivated—the financial upside of this role is meaningful, and the right candidate will be energized by it

• Own and grow a book of dealer accounts, selling across the full Cars Commerce suite:  marketplace, Dealer Inspire digital retailing and websites, Accu-Trade, and digital media solutions
• Lead discovery conversations at the dealer principal, GM, and marketing director level to understand each dealer’s operational and growth challenges
• Build tailored, multi-solution proposals that tie Cars Commerce products to measurable dealer outcomes (leads, inventory turn, digital retailing performance, trade acquisition efficiency)
• Manage complex, multi-stakeholder sales cycles from initial engagement through close and expansion

• Develop and execute account plans across your territory to maximize penetration and revenue per rooftop
• Identify whitespace—dealers not yet leveraging the full platform—and create pathways to deeper adoption
• Partner with Customer Success and Dealer Success Managers to ensure seamless onboarding and expansion post-sale

• Stay current on automotive retail trends, OEM programs, inventory market conditions, and competitive landscape to advise dealers as a credible industry consultant
• Serve as a trusted advisor to dealer groups and multi-rooftop accounts, building long-term relationships that insulate against competitive pressure

• Maintain rigorous pipeline, forecasting, and activity data in Salesforce—daily updates, accurate stage management, and 3–5x pipeline coverage
• Operate within a structured sales methodology (Sandler, Challenger, SPIN, MEDDIC, or equivalent) and articulate how you apply it
• Provide field-level market intelligence to product, marketing, and leadership teams
• Travel regularly within…