Senior Account Executive - Boston, MA

Senior Account Executive – Boston, MA

Candidates must reside in the territory.

We are building a next‑generation field sales organization. The Sr Account Executive is a consultative, solutions‑oriented senior seller who will diagnose dealership challenges and architect multi‑product solutions across the Cars Commerce portfolio. This high‑visibility individual contributor role has significant earning potential, direct field presence, and a mandate to elevate how we sell, deepen partner relationships, and grow revenue across dealer portfolios.

• 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 operational and growth challenges.
• Build tailored, multi‑solution proposals that link products to measurable dealer outcomes (leads, inventory turn, digital retailing performance, trade acquisition efficiency).
• Manage complex, multi‑stakeholder sales cycles from engagement through close and expansion.
• Develop and execute account plans to maximize penetration and revenue per rooftop.
• Identify whitespace and create pathways to deeper adoption.
• Partner with Customer Success and Dealer Success Managers for seamless onboarding and expansion post‑sale.
• Maintain rigorous pipeline, forecasting, and activity data in Salesforce with daily updates.
• Operate within a structured sales methodology (e.g., Sandler, Challenger, SPIN, MEDDIC) and articulate its application.
• Provide field‑level market intelligence to product, marketing, and leadership teams.
• Travel regularly within the territory; 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.
• Success selling complex, multi‑product, or platform solutions; not single‑SKU transactional sales.
• SaaS, digital media, or marketing technology sales background, especially in verticals with 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.
• Demonstrated consultative sales process: discovery, needs analysis, solution design, business case development, and close.
• Working command of a named sales methodology and demonstrable Salesforce rigor.
• Proficiency with CRM tools (Salesforce required) and virtual presentation platforms.

• Automotive experience combined with the required field sales 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 with ability to 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 in a field‑based, high‑volume territory model.
• Proficiency with CRM tools (Salesforce required) and virtual presentation platforms.

Structured as a 50/50 base/variable split reflecting seniority and scope. Uncapped commission potential tied to portfolio growth and new solution adoption. Car allowance or mileage reimbursement. Total target compensation range: $ – $.

• Medical, Dental & Vision healthcare plans.
• New Hire Stipend for Home Office set‑up.
• Generous PTO, paid holidays, floating holiday, volunteer day, recharge day.

• Applicants must be authorized to work in the United States; we are unable to sponsor employment visas.
• We are an equal‑opportunity employer and value diversity. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.