Sr. Product Manager - Insights & Advanced Analytics

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.

The Sr. Product Manager - Insights & Advanced Analytics is responsible for building and scaling Dealerware’s intelligence product line, transforming fleet data into monetizable intelligence embedded directly into the platform. This role sits at the intersection of data, economics, and product strategy, with accountability for turning operational fleet data into structured decision systems that improve capital efficiency, utilization, and revenue performance for dealership operators and OEM partners.

Enterprise reporting accuracy, consistency, and scalability are foundational to this role. Beyond that foundation, the mandate is to evolve reporting into forward-looking, decision-grade intelligence embedded directly into workflows. You will identify economically material problems within fleet operations, define the analytical frameworks required to solve them, and translate complex modeling into clear, actionable operator decisions.

This position carries direct responsibility for the reporting product roadmap, enterprise and OEM requirements, and the development of monetizable analytics capabilities tied to measurable customer impact. Success will be measured not only by feature delivery, but also by sustained adoption, revenue contribution, and demonstrable economic outcomes for customers.

The role reports directly to the Chief Product Officer and operates as a senior individual contributor with strategic visibility and commercial accountability across the organization.

Your work will directly impact lifecycle optimization, fleet sizing and mix decisions, revenue impact modeling for mobility programs, and causal measurement of downstream vehicle sales.

Product Scope and Accountability

You will own Dealerware’s reporting and intelligence product domain and be responsible for converting our data assets into structured, commercially viable products.

You will define and evolve the enterprise reporting roadmap, ensuring accuracy, consistency, and scalability across dealer groups and OEM stakeholders. This includes standardizing metrics, reducing custom report sprawl, and ensuring reporting supports accounting, compliance, and operational workflows. Reporting must be trusted, performant, and defensible.

You will identify economically material decision points within fleet operations and translate them into productized decision systems. This includes lifecycle optimization, utilization forecasting, pricing analysis, allocation risk, and revenue impact modeling. The expectation is not descriptive visibility but forward-looking, decision-grade capability embedded directly into the platform.

You will define packaging and pricing strategies for advanced analytics capabilities and validate willingness to pay before significant engineering investment. Success is measured by the financial impact on customers and the revenue contribution to Dealerware.

You will partner closely with Data and Platform Engineering to ensure data integrity and model robustness, and with Sales and Customer teams to drive adoption and expansion. You will operate independently with high ownership and strategic visibility.