The Ride Jobs in Boston, MA (NOW HIRING)

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 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.
What you'll do

• 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.

What you'll bring

• 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
• 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
• 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; familiarity with sales engagement and revenue intelligence platforms (e.g., Salesloft, Outreach, Gong) 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
$80,000-$100,000 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.
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