Escalations Account Executive

CarGurus · Boston, Massachusetts, United States

  • Senior
  • Full-time
  • $74,000 – $92,000
  • Posted 2026-08-30
  • Confirmed live on 25 September 2026

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Job description

Who we are

At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years.

What we do

The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride!

Role overview

The Escalations Account Executive is an action oriented sales role responsible for driving revenue recapture within our small independent dealership segment. In this position, you will focus entirely on managing a high volume portfolio of cancelled accounts, executing targeted sales activities to successfully win back and secure new commitments from former clients. This role requires an energetic sales professional with exceptional organization skills and a strong commitment to consistent daily outreach. You will build collaborative relationships with internal sales teams to gather quick insights and efficiently manage the sales process from initial contact to final contract execution. The primary objective is to drive down revenue churn and maximize re-won MRR through structured, high frequency sales execution.

What you'll do

• High Volume Revenue Recapture: Own and manage the end to end sales cycle to win back and re-sign former small independent dealerships through consistent outbound outreach.

• Internal Sales Team Collaboration: Build and maintain positive relationships with internal sales teams to quickly gather historical account insights and coordinate an effective outreach strategy.

• Structured Sales Execution: Deliver clear, ROI selling presentations designed to overcome common objections, address past dissatisfaction, and re-establish the value of CarGurus solutions.

• Contract Negotiation: Lead straightforward financial negotiations with small business owners and general managers to maximize re-won Monthly Recurring Revenue (MRR).

• Pipeline and Performance Management: Maintain a consistent and active pipeline of opportunities, ensuring exceptional CRM hygiene while moving small business accounts efficiently through the sales funnel to meet or exceed monthly sales goals.

• Activity Tracking and Forecasting: Maintain meticulous records of daily sales outreach while delivering accurate monthly forecasts on re-won revenue within the independent dealership segment.

• Competitive Awareness: Maintain a strong understanding of competitor offerings to effectively counter objections and position CarGurus as the premier digital marketing partner.

What you'll bring

• Inside Sales Track Record: Successful experience in a high activity inside sales or transactional SaaS environment, with a proven ability to manage a high volume sales funnel.

• Exceptional Organizational Skills: Strong time management capabilities with the ability to prioritize tasks and remain highly productive in a fast paced sales setting.

• Resilience and Stamina: A strong work ethic with the dedication to execute high volume outreach daily and maintain high energy across numerous sales conversations.

• Internal Relationship Building: Good interpersonal skills with the ability to collaborate effectively with internal sales and support teams.

• Overcoming Objections: Ability to confidently handle pushback, re-engage past small business clients, and guide them to a closed sale.

• Sales Tech Proficiency: High proficiency in Salesforce and modern sales outreach tools, utilizing data to manage a large pipeline efficiently.

• Results Driven Mindset: A strong sense of personal accountability for meeting sales targets, balanced with professional integrity and a competitive drive to succeed.

The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles.

Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training.

This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for disc

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