Principal Product Manager

Be essential at Cars Commerce At Cars Commerce, we’re fanatical about simplifying everything about car buying and selling. We do right by our customers and consumers to better connect the industry with simplified and tierless technology to enhance, measure and drive local automotive retail. Whether through our No.1 most recognized marketplace, Cars.com, our industry-leading digital experience, Dealer Inspire, our trade and appraisal technology, AccuTrade, our reputation-based digital wholesale auction marketplace, Dealerclub, or our new Cars Commerce Media Network, Cars Commerce is essential for success in the automotive industry. No one ever travels alone here: at its core, Cars Commerce is collaboration. In fact, it’s built into the very fabric of our shared values. We like to say we Rise Together – putting people at the center of what we do, from consumer to customer to community. Life at Cars Commerce makes it easy when we share the ethos to be Open to All, encouraging open-minded communication because we know diverse thinking yields better outcomes. But critical to our success is Caring to Challenge and Taking Ownership, fueling a competitive spirit in a respectful environment where we think about tomorrow but act today. At our foundation, we have integrity, Doing the Right Thing, even when it’s hard. It’s our shared commitment to these values that makes Cars Commerce a place where growth becomes not only possible, but downright unavoidable. But don't take our word for it. We are proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S. Ready to make your mark? Join a team that's driving real change in the automotive industry. About the role -  [Remote and must be located in Chicago area. May require onsite interviews] Join us in shaping a future of Automotive Commerce. Cars Commerce 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 Commerce — 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 Commerce ecosystem.  You will serve as the connective tissue between DI's product and engineering teams and key Cars Commerce 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 Commerce 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 credib