Escalations Account Executive

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.

What You Will Do

Own and manage the end-to-end sales cycle to win back and re-sign former small independent dealerships through consistent outbound outreach. Build and maintain positive relationships with internal sales teams to quickly gather historical account insights and coordinate an effective outreach strategy. Deliver clear, ROI selling presentations designed to overcome common objections, address past dissatisfaction, and re-establish the value of CarGurus solutions. Lead straightforward financial negotiations with small business owners and general managers to maximize re-won Monthly Recurring Revenue (MRR).

Why It Might Be a Fit

This role is ideal for a sales professional with a proven track record in high activity inside sales or transactional SaaS environments, with exceptional organizational skills and resilience for high volume outreach. You will have the opportunity to drive down revenue churn and maximize re-won MRR through structured, high frequency sales execution. The position offers a comprehensive Total Rewards Package including benefits, discretionary bonuses/incentives, and Restricted Stock Units (RSUs).

Requirements

• Successful experience in a high activity inside sales or transactional SaaS environment, with a proven ability to manage a high volume sales funnel
• Strong time management capabilities with the ability to prioritize tasks and remain highly productive in a fast paced sales setting
• A strong work ethic with the dedication to execute high volume outreach daily and maintain high energy across numerous sales conversations
• Good interpersonal skills with the ability to collaborate effectively with internal sales and support teams
• Ability to confidently handle pushback, re-engage past small business clients, and guide them to a closed sale
• High proficiency in Salesforce and modern sales outreach tools, utilizing data to manage a large pipeline efficiently
• A strong sense of personal accountability for meeting sales targets, balanced with professional integrity and a competitive drive to succeed

Benefits

• Equity for all employees
• Flexible hybrid model
• Robust time off policies
• Daily free lunch
• New car discount
• Meditation and fitness apps
• Commuting cost coverage
• Discretionary bonuses/incentives
• Restricted Stock Units (RSUs)