Escalations Account Executive

Escalations Account Executive

Boston, MA August 31, 2026

At CarGurus, 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.

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 CarGurusour 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 discretionary bonuses/incentives and Restricted Stock Units (RSUs).

Position Pay Range $1 $1 USD

We reward our Gurus' curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives.

CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate.

CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potentialstarting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That's why we hope you'll apply even if you don't check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus.

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