Sr. Account Executive - Central & Western Massachusetts

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!