Principal Product Manager

Cars.com•Chicago, IL

5d•Remote

About The Position

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.

Requirements

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.

Nice To Haves

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).

Responsibilities

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.
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.
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.
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.