Principal Product Manager

Power confident decisions at Cars.com Cars.com is the marketplace millions of people trust to buy and sell cars with confidence. More than 25 years ago, we started as a simple idea, connect buyers and sellers, and today we do a lot more: trusted reviews, transparent pricing, and real-time, proprietary data that cut through the noise of one of life's biggest purchases. Our scaled marketplace, paired with interconnected technology, data, and media, gives dealers and OEMs everything they need to sell more cars. At Cars.com, we debate openly, decide fast, and deliver what we say we will.

We solve real problems for car shoppers and dealers, simplify for speed, and focus on what matters most. We win together or not at all. Here, your work counts, your ideas can help shape what’s next, and you’ll build alongside people who have your back. We’re in the middle of a real transformation, modernizing the company and investing in AI and data to move faster. You're joining the No. 1 brand people think of first when shopping for a car, at the exact moment it's being rebuilt for what's next. You help decide what that becomes.

That kind of influence is rare, and it's exactly why this is a place worth building your career. Don't just take our word for it, we're proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S. Ready to help build the most trusted place to buy and sell a car? Join us. This role is remote, with priority given to candidates based in Chicago (IL) and Austin (TX). Onsite interviews may be required. About the role Join us in shaping a future of Automotive Commerce. Cars.com builds solutions for automotive dealerships, manufacturers, and consumers.

Our driving force is to deliver a single platform that simplifies everything about buying and selling cars. Our Websites Product Team drives our ‘Dealer Inspire’ platform. Dealer Inspire (DI) is a leading automotive website and technology platform serving thousands of dealerships across the United States. DI is part of Cars.com — an industry-leading platform that includes Cars.com, AccuTrade, and other brands — giving DI the reach, data, and ecosystem depth to build products that move the industry forward.

We are on a transformational journey, building innovative services that redefine how we deliver value to our customers. As a Principal Product Manager on our Websites Product Team, you will shape the future of our platform — driving a comprehensive product strategy to simplify, scale, and make a lasting impact within the automotive industry. Our data-driven products are at the core of the Dealer Inspire platform.

We seamlessly link shoppers across Cars.com and Dealer Inspire websites — acquiring, transforming, and analyzing data that empowers our teams to turn information into meaningful insights and outcomes to make an impact within the automotive industry.

About you - Our Principal Product Manager role is an independent contributor leadership role and most senior product role in DI This is an exceptional opportunity to influence the future of our DI Platform As a Principal Product Manager, you will own our most strategic and complex product initiatives that require navigating organizational complexity, spanning multiple business units, and delivering meaningful, lasting value for our dealer customers and the broader Cars.com ecosystem.

You will serve as the connective tissue between DI's product and engineering teams and key Cars partners — including Cars.com, AccuTrade, and D2C Media — leading work at the intersection of ambitious product vision and organizational reality. This means driving alignment across teams, managing stakeholders with competing priorities, and supporting a customer base that depends on your platform every day.

You are a seasoned product leader fluent in both platform evolution and AI product strategy — identifying where LLM-powered, generative, and predictive capabilities create real leverage for DI's products and dealers. You know how to bring customers through meaningful change with clarity and confidence. As a Principal PM, you are a coach to the DI PM team, a trusted thought partner to engineering leadership, and a credible voice at the executive level — setting the bar for what great product work looks like at Dealer Inspire.

Why You'll Be Excited About This Role This opportunity enables you to.. Strategic Product Leadership Own the product vision and roadmap for some of DI's most strategic and complex initiatives, including next-generation platform capabilities and features that differentiate DI in the market. Define and sequence high-impact initiatives that balance near-term dealer value delivery against long-term product and platform goals, making clear trade-offs between scope, risk, and business impact.

Drive internal alignment across DI product, engineering, and leadership — ensuring all stakeholders share a clear, credible, and consistently communicated view of where we're going and why. Develop customer-facing strategies for significant product changes, working with account management, sales, and marketing to communicate in ways that build dealer confidence and trust.

Cross-Platform Product Leadership Serve as a PM interface into Cars business units — Cars.com, AccuTrade, D2C Media, and others — identifying and owning cross-platform initiatives that create the most compounding value across the ecosystem. Define clear, interconnected roadmaps across DI and partner platforms, surfacing dependencies and aligning on intersection points before they become blockers. Navigate organizational complexity and competing priorities across business units with credibility, empathy, and a bias toward resolution.

AI & Innovation Strategy Strongly contribute to AI product strategy for Dealer Inspire — identifying where LLM-powered, generative, and predictive capabilities create genuine dealer and consumer value, and building the case and roadmap for their development. Work closely with DI engineering to evaluate AI/ML approaches, ensure responsible and high-quality implementation, and deliver AI features that perform in production at scale. Stay ahead of the competitive landscape in automotive digital retail and AI/LLM tooling, bringing insight that shapes DI's strategic direction.

Craft & Team Elevation Define and deliver the roadmap for strategic initiatives, operating independently and with a clear line of sight from initiative to business outcome. Be a hands-on coach and mentor to the DI PM team, elevating the team's ability to handle complexity, ambiguity, and strategic product challenges. Set the gold standard for problem definition, discovery, and roadmap communication at Dealer Inspire.

Partner deeply with DI Engineering leadership to ensure tight alignment between product vision and technical execution, actively participating in architecture conversations and trade-off decisions. Refine and contribute to team-level goals (KPIs/OKRs) and communicate progress, impact, and opportunities effectively to senior leadership. We're Excited About You Because… Bachelor's degree in business, computer science, economics, or a related field — or equivalent experience.

10+ years of product management experience, with a track record of delivering high-impact outcomes across complex, multi-stakeholder product environments. Experience with B2B SaaS solutions, ecommerce, and scalable website platforms. Demonstrated experience leading significant platform evolution or major product transitions including managing the organizational and customer-facing dimensions, not just the technical ones.

Strong change management skills: you have successfully navigated internal alignment challenges and brought external customers through meaningful product transitions with confidence and clarity. Meaningful experience in AI/LLM product strategy — you have shipped AI-powered product features and can evaluate technical approaches, articulate trade-offs, and build compelling product cases around AI capabilities. Proven ability to operate across organizational boundaries, aligning multiple teams, business units, or partners toward shared goals on complex, cross-platform initiatives.

Exceptional communication and storytelling skills, including strong executive presence and comfort presenting to VPs and ELT [Executive Leadership Team] audiences. Strong analytical skills and commitment to data-driven decision-making, experimentation, and customer research, balanced with sound product intuition. Experience working across the full product lifecycle, from strategy and discovery through delivery, optimization, and sunset. Bonus - MBA or other advanced degree. Experience in automotive technology, dealer operations, digital retailing, financing.

Experience as a software engineer or a technical product role. Experience working within a multi-brand or platform ecosystem (e.g., parent company / subsidiary structures, marketplace + SaaS hybrid businesses). Compensation We share compensation up front so you have the information you need to make a confident decision. This range reflects target base compensation. Where you land depends on skills and experience. If this range works for you, we encourage you to apply. Salary Range: $175,800.00-219,750.00 Benefits Confidence, built in.

The same confidence we build for car buyers and sellers, we build into how we treat our own: Medical, dental & vision from day one — no waiting period 401(k) with company match, immediate vesting Employee Stock Purchase Plan — buy Cars.com stock at a discount Unlimited Flex Time Off, 11 paid holidays, 1 volunteer day Paid parental and caregiver leave $350 one-time home office stipend + $70/month for virtual-first work Tuition reimbursement up to $5,250/year ...and more — see our full Benefits, Perks & Culture here Legal For US-based positions: Applicants must be authorized to work in

the United States. We're unable to sponsor employment visas at this time. Cars.com is an equal opportunity employer and values diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Applicants: click here to review our Privacy Policy for Applicants. Current employees: click here to review our California Privacy Policy for Employees. Cars.com is a leading marketplace for automotive sales.

For over 25 years, we've helped millions of people cut through the noise and make real decisions about buying and selling cars. Behind that is a team that genuinely loves solving hard problems — for shoppers, for dealers and automakers, and for each other. Brand & sub-brands U.S. Cars.com: You'll work under the Cars.com name. U.S. Dealer Inspire: You'll work for Cars.com, but build our Dealer Inspire technology. Dealer Inspire is owned by Cars.com and serves as our digital experience sub-brand for dealers in the U.S.

Canada: You'll work for Cars.com, but build our D2C Media technology for the Canadian market. D2C Media is owned by Cars.com and serves as our digital experience brand in Canada. We're building trust in an industry that has historically struggled with it. We give shoppers clarity and certainty in one of life's biggest purchases, and we give dealers and automakers a marketplace and the technology that actually grows their business. Cars.com is in the middle of a real transformation — modernizing the company, investing in AI and data, and moving faster than ever.

We have a powerful brand name and all the ingredients needed to win. What we don't have yet is everyone we need to get there. That's where you come in. We are looking for strong talent to help build what’s next.