Senior Product Leader — AI-Driven Automotive Platform (Remote)

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

• 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 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).

In the spirit of pay transparency, we are excited to share the base salary range for this position. In addition to base salary, some roles are eligible for our bonus and/or equity programs, depending on level and role. Regular full-time positions are eligible for our comprehensive benefits package. If you are hired at Cars Commerce, your final base salary compensation will be determined based on factors such as skills and/or experience.

Salary Range $175,800.00-219,750.00

Our Comprehensive Benefits Package includes:

• Medical, Dental & Vision Healthcare Plans
• New Hire Stipend for Home Office Set-Up
• Generous PTO Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day
• Learn more about our Benefits, Perks, & Culture on our LinkedIn Life Pages!

For US-based Positions: Applicants must be authorized to work in the United States. Please note that we are unable to sponsor employment visas at this time.

We are an equal opportunity employer and value 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.

Welcome! At Cars Commerce, we think big, push boundaries, and rise together as a team. It’s all the challenge and energy of a job in the tech industry, backed by 25 years of proven resilience and growth as a leading consumer brand. Imagine getting to work on a team with a bold mission to simplify everything about buying and selling cars. A culture that’s a unique mix of innovation and collaboration. Exciting training and development opportunities that empower you to take ownership of your career. For our employees, every day is an opportunity. We’re a remote-first workplace that embraces diversity at every level. Inspired by our values, we intentionally create opportunities for our employees to grow and make an impact in our industry and local communities. Let’s move your career forward together.

Cars Commerce is an audience-driven technology company empowering automotive that simplifies everything about buying and selling cars. The Cars Commerce platform includes the flagship automotive marketplace and dealer reputation site Cars.com, innovative digital marketing technology and services from Dealer Inspire, industry-leading trade-in and appraisal technology from AccuTrade, an exclusive in-market media network, and powerful and predictive AI technologies that enable more efficient and profitable retail operations. Cars Commerce is the essential partner to stay one step ahead in automotive.