Vice President, Inside Sales

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 Vice President, Sales (Inside Sales) to lead and scale a large, high-velocity sales engine into its next phase of growth. This leader will balance strategic foresight with hands-on leadership, ensuring the team consistently delivers double-digit revenue growth while evolving toward a more value-based, consultative sales motion. The VP will be accountable for designing the operating model, optimizing productivity, driving cross-sell and retention, and fueling morale and energy across a 200+ person organization that generates more than $500M in annual revenue.

Success requires a performance-oriented operating rhythm, a bias for innovation, and the ability to drive change management with clarity and confidence, translating strategy into execution at scale while guiding the team through transformation.

What you’ll do

Strategy & Operating Model

• Design and evolve a scalable inside sales strategy to support CarGurus’ marketplace, software and data offerings.

• Redesign organization structure toward regionalization across ~30 markets, ensuring optimal coverage, accountability, and alignment with field sales.

• Partner with the CRO and executive team to set the “what,” and own the “how” with the inside sales team, testing, learning, and iterating quickly.

Sales Motion & Process Maturity

• Transition the organization from a transactional model to a value-based, consultative sales approach while maintaining high velocity.

• Standardize discovery, qualification, and business case development, raising process maturity and embedding best practices across teams.

• Shift success metrics from monthly bookings to net MRR, with leading indicators integrated across the funnel.

Productivity & Performance Management

• Maintain and expand rep productivity at six to eight new deals per month per seller (~$2K MRR each).

• Implement rigorous coaching, enablement, and inspection rhythms to drive consistency across tenure levels.

• Employ AI and scalable tools, dashboards, and operating cadences to improve forecasting, throughput, and accountability.

Growth & Retention

• Expand cross-sell and upsell across CarGurus’ dealer product portfolio, including Listings, RPM, and Digital Deal.

• Reduce ~20% annual churn by implementing targeted save plays, lifecycle engagement, and account health programs.

• Build strategies that unlock new revenue streams and increase wallet share per dealer.

Collaboration & Leadership

• Hire, develop, and inspire a premier leadership bench across sales management levels.

• Partner cross-functionally with Product, Marketing, Operations, and Finance to align on dealer value creation.

• Foster a high-performance, high-morale culture grounded in collaboration, accountability, and learning.

What you’ll bring

• Proven track record leading large, high-velocity inside sales organizations ($200M–$600M+ revenue scale).

• Demonstrated success evolving transactional models into value-based selling without sacrificing throughput.

• Expertise in regionalization, geo-coverage design, and inside/field sales coordination.

• Experience driving multi-product growth and cross-sell strategies in SaaS, marketplace, or subscription models.

• Strong analytical and data-driven operator; fluent in dashboards, unit economics, and net MRR metrics.

• Depth in change management, with evidence of successful “what got us here won’t get us there” transformations.

• Dynamic communicator and catalyst for impact; equally comfortable setting strategy and energizing front-line teams.

Who you are

• Catalyst for impact with a bias for action and an ability to simplify complexity.

• Change leader who thrives in ambiguity and fast-moving environments.

• Collaborative partner who builds inclusion, trust, and strong cross-functional alignment.

• Decisive, accountable executive who makes clear, timely decisions to drive execution.

• A motivational and transformational leader who listens and connects at every level, inspires confidence, and aligns the organization around shared goals to drive results.

• A dynamic presence who can push for performance while fostering a culture of collaboration through creating energy and urgency, celebrating wins, addressing challenges directly, and rallying the team to push harder and win together.

• Values aligned with CarGurus: pioneering, transparent, data-driven, fast-moving, collaborative, and ethical.

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
$368,000—$460,000 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