Escalations Account Executive

CarGurus•Boston, MA

8d•Hybrid

About The Position

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.

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.

Responsibilities

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).
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.
Maintain meticulous records of daily sales outreach while delivering accurate monthly forecasts on re-won revenue within the independent dealership segment.
Maintain a strong understanding of competitor offerings to effectively counter objections and position CarGurus as the premier digital marketing partner.