Senior Sales Specialist

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
CarGurus is seeking a Senior Sales Specialist to join our growing Inventory Pillar and help shape how dealerships manage, price, stock, merchandise, and optimize their vehicle inventory. In this high-impact role, you will accelerate the adoption of PriceVantage and StockVantage while serving as a key commercial resource for the future expansion of our broader Inventory Management Solutions.
Working as a product-focused seller and subject-matter expert, you will partner closely with Account Executives, Regional Sales Directors, and Product leaders to identify opportunities, engage dealership decision-makers, and drive qualified deals to close. While Account Executives own the primary dealer relationship, you serve as the specialized hunter for the Inventory Pillar. Success requires establishing instant credibility with Dealer Principals, General Managers, and Used Car Managers by quickly assessing their operations, respectfully challenging entrenched workflows, and articulating how CarGurus enables faster, more profitable inventory decisions.
The ideal candidate is a confident, accountable automotive sales professional who thrives in a fast-paced environment and takes ownership of clear revenue and activity targets. Beyond selling existing solutions, you will act as a collaborative builder-synthesizing market feedback from dealer meetings, influencing future product capabilities, refining go-to-market strategies, and helping shape the future of CarGurus Inventory Management. Travel is required for dealer meetings, strategic sales opportunities, industry events, and internal collaboration.
What you'll do

• Partner closely with Account Executives and Regional Sales Directors to develop and execute Inventory Management opportunities across their dealer portfolios.
• Lead discovery conversations with dealer principals, general managers, used vehicle managers, internet directors, and other key decision-makers.
• Deliver compelling product demonstrations that connect CarGurus Inventory Management capabilities directly to a dealer's operational challenges and business objectives.
• Own the specialist portion of the sales cycle, including discovery, demonstration, objection handling, negotiation, and closing.
• Help AEs and RSDs identify the right customers, buying personas, and opportunities for CarGurus Inventory Management solutions.
• Build strong working relationships with assigned sales teams and proactively develop strategies to increase opportunity creation, pipeline, and closed revenue.
• Confidently position CarGurus Inventory Management solutions against established dealership pricing, merchandising, and inventory management platforms.
• Use dealership knowledge and an analytical approach to challenge existing inventory strategies and help customers think differently about how they price, merchandise, source, and manage vehicles.
• Become a subject-matter expert across PriceVantage, StockVantage, and future CarGurus Inventory Management products as the portfolio continues to evolve.
• Travel as needed to support strategic dealer opportunities, in-person presentations, industry events, and other business needs.
• Maintain strong pipeline discipline, opportunity management, and forecasting within Salesforce.
• Share successful talk tracks, objection-handling strategies, competitive insights, and best practices across the Sales Specialist and broader sales organization.
• Serve as a critical voice of the dealer by providing thoughtful market feedback to Product, Product Marketing, Strategy, Sales Leadership, and other cross-functional partners.
• Partner closely with Product and go-to-market teams as new Inventory Management capabilities are developed, tested, and brought to market.
• Stay current on automotive retail trends, dealership inventory challenges, competitive products, and evolving dealer needs.
• Consistently achieve or exceed monthly and quarterly sales targets.

What you'll bring

• 5+ years of sales or sales leadership experience, including a demonstrated ability to close business and lead negotiations.
• 3+ years of automotive industry experience required, preferably selling directly to dealerships.
• Direct dealership retail experience is strongly preferred, particularly in used vehicle operations, inventory management, pricing, merchandising, or dealership leadership.
• Strong understanding of dealership operations and the ability to communicate credibly with dealer owners, general managers, used vehicle managers, and other senior dealership personnel.
• Proven track record of consistently achieving or exceeding revenue targets.
• Strong discovery, presentation, demonstration, objection-handling, and closing skills.
• Ability to operate successfully within a collaborative or overlay sales model where account ownership is shared across multiple stakeholders.
• Strong analytical skills and the ability to translate data and insights into a compelling business story.
• Comfort operating in an evolving product environment and bringing new solutions to market.
• Excellent organization, pipeline management, forecasting, and communication skills.
• Self-motivated, competitive, adaptable, and comfortable operating with a high degree of autonomy.
• Ability to provide clear, constructive customer and market feedback to cross-functional teams.
• Willingness and ability to travel as needed to support dealer meetings, strategic opportunities, industry events, and internal business needs.
• Salesforce experience is strongly preferred.

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
$160,000 - $200,000 USD
Working at CarGurus
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.
We welcome all
CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential-starting 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. #LI-Hybrid