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About the Role
Cars Commerce is seeking a Principal Product Manager to shape the future of the Dealer Inspire platform. This role involves driving product strategy, simplifying and scaling services, and making a lasting impact within the automotive industry by leveraging data-driven products and AI capabilities.
Responsibilities
- Own the product vision and roadmap for strategic and complex initiatives, including next-generation platform capabilities.
- Define and sequence high-impact initiatives balancing near-term dealer value with long-term product and platform goals.
- Drive internal alignment across product, engineering, and leadership teams.
- Develop customer-facing strategies for significant product changes.
- Serve as a Product Manager interface into Cars Commerce business units (Cars.com, AccuTrade, D2C Media).
- Define clear, interconnected roadmaps across DI and partner platforms.
- Contribute to AI product strategy for Dealer Inspire, identifying opportunities for LLM-powered, generative, and predictive capabilities.
- Work closely with engineering to evaluate AI/ML approaches and ensure high-quality implementation.
- Stay ahead of the competitive landscape in automotive digital retail and AI/LLM tooling.
- Define and deliver the roadmap for strategic initiatives, operating independently.
- Coach and mentor the DI PM team, elevating their ability to handle complexity and strategic challenges.
- Set the standard for problem definition, discovery, and roadmap communication at Dealer Inspire.
- Partner with DI Engineering leadership to ensure alignment between product vision and technical execution.
- Refine and contribute to team-level goals (KPIs/OKRs) and communicate progress to senior leadership.
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.
- Strong change management skills.
- Meaningful experience in AI/LLM product strategy, including shipping AI-powered product features.
- Proven ability to operate across organizational boundaries, aligning multiple teams, business units, or partners.
- Exceptional communication and storytelling skills, including strong executive presence.
- Strong analytical skills and commitment to data-driven decision-making, experimentation, and customer research.
- Experience working across the full product lifecycle, from strategy and discovery through delivery, optimization, and sunset.
- MBA or other advanced degree (Bonus).
- Experience in automotive technology, dealer operations, digital retailing, financing (Bonus).
- Experience as a software engineer or a technical product role (Bonus).
- Experience working within a multi-brand or platform ecosystem (Bonus).
- Applicants must be authorized to work in the United States.
- Unable to sponsor employment visas at this time.
Skills
- Platform evolution
- AI product strategy
- LLM-powered capabilities
- Generative capabilities
- Predictive capabilities
- B2B SaaS
- Ecommerce
- Scalable website platforms
- Change management
- AI/LLM product strategy
- Executive presence
- Data-driven decision-making
- Product lifecycle management
Location
- Remote
- Chicago area
Work Type
- Remote
Experience Level
- Principal
- 10+ years of product management experience
Education Level
- Bachelor's degree in business, computer science, economics, or a related field, or equivalent experience.
Salary/Compensations
- $175,800.00 - $219,750.00
Benefits
- Medical, Dental & Vision Healthcare Plans
- New Hire Stipend for Home Office Set-Up
- Generous PTO
- Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day
About the Company
- Cars Commerce is fanatical about simplifying everything about car buying and selling, connecting the industry with simplified and tierless technology.
- Brands include Cars.com, Dealer Inspire, AccuTrade, Dealerclub, and Cars Commerce Media Network.
- Values include Rise Together, Open to All, Caring to Challenge, Taking Ownership, and Doing the Right Thing.
- Named one of Built In's 2026 Best Places to Work in Chicago and across the U.S.
Equal Opportunity
- 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.