Principal Product Manager

Cars Commerce•Chicago, IL

6d•$175,800 - $219,750•Remote

About The Position

Join Cars Commerce and shape the future of Automotive Commerce. Cars Commerce builds solutions for automotive dealerships, manufacturers, and consumers, aiming to deliver a single platform that simplifies everything about buying and selling cars. The Websites Product Team drives the Dealer Inspire (DI) platform, a leading automotive website and technology platform serving thousands of dealerships. As part of Cars Commerce, DI benefits from the reach, data, and ecosystem depth of brands like Cars.com and AccuTrade. This role is on a transformational journey, building innovative services to redefine value delivery. As a Principal Product Manager on the Websites Product Team, you will shape the future of the DI platform by driving a comprehensive product strategy to simplify, scale, and make a lasting impact within the automotive industry. The data-driven products are central to the DI platform, seamlessly linking shoppers across Cars.com and DI websites by acquiring, transforming, and analyzing data to empower teams with meaningful insights and outcomes.

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.
Strong change management skills: successfully navigated internal alignment challenges and brought external customers through meaningful product transitions.
Meaningful experience in AI/LLM product strategy — shipped AI-powered product features and can evaluate technical approaches, articulate trade-offs, and build compelling product cases.
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 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.
Define and sequence high-impact initiatives that balance near-term dealer value delivery against long-term product and platform goals.
Drive internal alignment across DI product, engineering, and leadership.
Develop customer-facing strategies for significant product changes, working with account management, sales, and marketing.
Serve as a PM interface into Cars Commerce business units (Cars.com, AccuTrade, D2C Media, etc.), identifying and owning cross-platform initiatives.
Define clear, interconnected roadmaps across DI and partner platforms, surfacing dependencies and aligning on intersection points.
Navigate organizational complexity and competing priorities across business units.
Contribute to AI product strategy for Dealer Inspire, identifying where LLM-powered, generative, and predictive capabilities create dealer and consumer value.
Work closely with DI engineering to evaluate AI/ML approaches, ensure responsible implementation, and deliver AI features at scale.
Stay ahead of the competitive landscape in automotive digital retail and AI/LLM tooling.
Define and deliver the roadmap for strategic initiatives, operating independently.
Act as a hands-on coach and mentor to the DI PM team.
Set the standard for problem definition, discovery, and roadmap communication at Dealer Inspire.
Partner deeply 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.