Sr. Product Manager - Insights & Data Intelligence

About Dealerware

Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible.

In 2026, Dealerware was recognized by Built In as one of their Best Startups to Work for in Austin for the fifth consecutive year.

As Sr. Product Manager - Insights & Data Intelligence
, you will shape how the automotive industry understands, predicts, and optimizes fleet behavior
—turning millions of daily vehicle, transaction, and operational signals into intelligence that dealers, dealer groups, and OEMs can act on with confidence.

This role sits at the intersection of automotive innovation, customer insight, and applied AI
. You’ll define how insights are surfaced, how intelligence is embedded into workflows, and how emerging AI capabilities—such as predictive analytics, anomaly detection, and natural language insights—can help automotive operators move faster, operate smarter, and unlock new revenue opportunities.

If successful, your work will help customers answer questions like:

• Which vehicles should I keep, rotate, or retire—and when?
• What’s the right fleet size and model mix for my market?
• How much incremental revenue could be unlocked by formalizing a retail rental program beyond service-only customers?
• Are courtesy and extended drive programs driving repeat purchases and incremental new car sales?

This role reports to the Sr. Director of Product Management and partners closely with Data Engineering, Customer Success, Sales, and Partnerships.

• Partner with the VP of Data Engineering to drive a company-wide, insight-driven mindset.
• Define a product vision that evolves Dealerware from reporting → insights → intelligence.
• Develop pricing and packaging strategies that monetize insights by delivering clear, outcome-driven value to customers.
• Lead the end-to-end lifecycle of insights and analytics products—from ideation and discovery to launch and iteration.
• Translate complex datasets into intuitive dashboards, workflows, and intelligence surfaces that customers actually use.
• Ensure high standards for accuracy, usability, and adoption—not just delivery.
• Engage directly with dealerships, dealer groups, and OEMs through discovery calls, on-site visits, and ongoing research.
• Identify jobs-to-be-done and decision points where insights can materially change outcomes.
• Post-launch, measure adoption and impact, and partner with Customer Success, Sales, and Marketing to drive sustained usage.
• Design reporting and insights that support accounting workflows, compliance needs, and operational decision-making.
• Balance financial rigor with usability for non-technical users.
• Collaborate with engineering, design, marketing, sales, customer success, and partnerships.
• Influence without authority, aligning teams around a shared insights vision.
• Track competitive and industry trends in automotive analytics, AI, and fleet intelligence.
• Identify opportunities to apply AI/ML (predictive analytics, natural language summaries, anomaly detection, automation) to customer problems.
• Champion experimentation that moves Dealerware ahead of traditional BI and static reporting.
• Balance ambition with pragmatism—shipping value early and often.
• Rally teams around your vision and create momentum across the organization.
• Navigate trade-offs thoughtfully, always looking for win-win outcomes.

• Insights products are adopted, not just launched: Key dashboards, reports, and intelligence features show strong usage, repeat engagement, and expansion across customer segments.
• Dealerware has moved beyond “reporting”: The platform delivers predictive, proactive, or automated insights—not just real-time and historical views.
• Clear business impact is measurable: Insights contribute to improved…