Associate Sales Specialist

CarGurus • Boston, MA

19h • Hybrid

About The Position

CarGurus has identified strong market fit for a product that launched last Fall. The CarGurus Pricing Tool is sold into a different part of the dealership and to a different buying persona than our core products. As we scale this product's go-to-market motion, we are seeking an experienced, strategic pipeline development professional to independently drive qualified opportunity generation for our growing team of Sales Specialists. This is not an entry-level position. We are looking for an experienced sales professional who operates with a high degree of autonomy and can develop and execute account-level prospecting strategies, engage senior dealership decision-makers with consultative credibility, and generate a high volume of qualified demos across a complex, multi-stakeholder selling environment. You will own the top-of-funnel pipeline engine for a strategic growth product, working cross-functionally with Field Sales, Inside Sales, Account Management, Product, and Sales leadership to accelerate market penetration. For this role, we're able to hire in any state within the continental United States.

Requirements

• 3–5+ years in a sales development, inside sales, or full-cycle sales role with a demonstrated record of exceeding quota in high-volume outbound environments
• Proven ability to engage senior decision-makers through cold outreach at volume, with the consultative credibility to navigate complex dealership organizational structures
• Highly autonomous and strategic; capable of independently building account plans, developing messaging, and managing pipeline with minimal oversight
• Strong analytical, organizational, and communication skills with the ability to synthesize market intelligence and present insights to cross-functional leadership
• Numbers-driven, with a competitive mindset and a genuine commitment to outbound pipeline generation as a professional discipline
• Salesforce.com experience required

Nice To Haves

• Experience selling into the automotive industry strongly preferred but not required; direct dealership experience or specialized knowledge of inventory management and pricing workflows is a significant plus
• familiarity with sales engagement and revenue intelligence platforms (e.g., Salesloft, Outreach, Gong) preferred

Responsibilities

• Independently develop and execute outbound prospecting strategies to generate a high volume of qualified product demos for Sales Specialists, directly influencing revenue growth for a strategic product line.
• Design and manage targeted account plans, identifying high-value dealer segments based on competitive landscape analysis, product fit signals, and market opportunity data.
• Partner cross-functionally with Sales Specialists, AEs, AMs, and Sales leadership to identify pipeline opportunities across their portfolios, applying consultative engagement to secure meetings with senior dealership stakeholders including General Managers, Used Car Directors, and Inventory Managers.
• Own the development and iteration of outbound playbooks
• Maintain rigorous pipeline management in Salesforce, ensuring data integrity across all outreach activity, lead qualification, and opportunity progression.
• Serve as a strategic feedback channel to Product, Product Marketing, and Sales Strategy by translating objection patterns, competitive intelligence, and market signals into actionable insights for cross-functional stakeholders.

Benefits

• equity for all employees, both when they start and as they continue to grow with us
• career development and corporate giving programs
• employee resource groups (ERGs) and communities
• flexible hybrid model
• robust time off policies
• daily free lunch
• new car discount
• meditation and fitness apps
• commuting cost coverage

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed