[Remote] Principal Product Manager

Note: The job is a remote job and is open to candidates in USA. Cars.com LLC, operating through Cars Commerce and Dealer Inspire, is hiring a Principal Product Manager to shape the Dealer Inspire platform’s product strategy and roadmap. The role leads complex cross-platform initiatives, advances AI product strategy, and aligns product, engineering, business partners, and customers around platform evolution.

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

Skills

• 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
• 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
• Applicants must be authorized to work in the United States
• We are unable to sponsor employment visas at this time
• 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)

Benefits

• Medical, Dental & Vision Healthcare Plans
• New Hire Stipend for Home Office Set-Up
• Generous PTO
• Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day
• Remote work; must be located in Chicago area.

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