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, 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.

Senior Account Executive

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 is a high-visibility individual contributor role with 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:

Our DRIVE Competency Model

• 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: Cars.com 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 be able to articulate how you apply it

• Provide field-level market intelligence to product, marketing, and leadership teams

• Travel regularly within your territory; this is a road-warrior role with frequent in-person dealer visits expected

• 8+ years of B2B field sales experience with a documented, multi-year track record of meeting or exceeding quota

• Demonstrated success selling complex, multi-product or platform solutions — not single-SKU transactional sales

• SaaS, digital media, or marketing technology sales background, particularly in verticals with high SMB-to-enterprise dealer or franchisee dynamics

• Comfort operating in a high-activity, travel-intensive field role calling on business owners and senior dealership leadership

• Proven ability to run a consultative sales process: discovery, needs analysis, solution design, business case development, and close

• Working command of a named sales methodology and demonstrable Salesforce rigor

• Automotive, if combined with the above required experience

• Experience selling to multi-rooftop dealer groups or large franchise accounts

• Familiarity with automotive retail metrics (VDP views, leads, conversion rates, trade funnels, digital retailing workflows)

• Executive presence — ability to build credibility quickly with dealer principals and GMs

• Strong business acumen; can translate platform capabilities into dealer P&L impact

• Natural curiosity and active listening; asks great questions before pitching

• Unapologetically money-motivated — driven by the earning upside this role provides

• Resilience and self-motivation suited to a field-based, high-volume territory model

• Proficiency with CRM tools (Salesforce required) and virtual presentation platforms

Compensation structured as a 50/50 base/variable split reflecting the seniority and scope of this role.

• Uncapped commission potential tied to portfolio growth and new solution adoption

• Car allowance or mileage reimbursement

• Access to the full Cars Commerce product portfolio as a sales professional — you’ll sell tools that genuinely move the needle for dealers

Cars Commerce is at an inflection point. We have the broadest product portfolio in our history — marketplace, websites, trade, and media — and we are restructuring our commercial organization to sell that portfolio the way it deserves to be sold: as an integrated platform with real dealer ROI at its center. The Senior Account Executive role is the commercial face of that transformation. If you are a seasoned seller who is energized by complexity, motivated by significant earning potential, and excited to help shape a new sales motion at scale, this is your moment.

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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