Account Executive - Fairfield, CT

About the Role

Cars Commerce is looking for a driven, disciplined Account Executive who embodies our DRIVE values: Disciplined, Results-Proven, an Interconnected Solution Seller, Voraciously Hungry, and Earning-Motivated. This is a field-based, quota-carrying role for a seasoned seller who runs their book like a business and is unapologetically motivated to win and earn. Candidates must reside within the assigned territory (Litchfield, New Haven, & Westchester Counties) and be able to travel by car for face-to-face visits with existing and prospective customers.

What You'll Do

• 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.

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.

Pay

Total Target Compensation Range: $118,600.00 – 148,250.00 (base salary + variable).

Benefits

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