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Dealerware transforms the automotive retailers of today into the mobility network of tomorrow.
The Role
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.
Enterprise Reporting
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.
Productized Intelligence
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.
Monetization & Economic Impact
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.
Cross-Functional Execution
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.
What Success Looks Like:
- Analytics and intelligence are established as a meaningful revenue driver for Dealerware, with multiple monetized capabilities generating expansion revenue and validated pricing power across customer segments.
- Enterprise reporting is trusted, standardized, and scalable across dealer groups and OEM partners, with consistent metric definitions and minimal reliance on custom builds.
- Dealerware delivers decision-grade intelligence that measurably improves customer economics, including capital efficiency, utilization, margin performance, or incremental revenue, with documented ROI.
- Advanced analytics capabilities, including predictive or AI-driven components, are deployed in production, embedded within workflows, and deliver sustained operational impact rather than isolated reporting features.
About You:
- You are a product leader who thinks in systems, not features. You are comfortable working with complex datasets, economic trade-offs, and probabilistic outcomes, and you can translate that complexity into clear, structured decisions for non-technical operators.
- You have experience shipping analytics or intelligence products that change customer behavior, not just surface information. You understand that reporting is foundational, but real value comes from embedding forward-looking insight directly into operational workflows.
- You are commercially disciplined. You validate demand before building at scale, define pricing intentionally, and measure success in financial terms. You are comfortable being accountable for revenue impact, not just roadmap delivery.
- You operate independently with strong judgment and high ownership. You influence engineering, design, and go-to-market partners through clarity of thinking and rigor, not volume.
- You are motivated by building product lines that generate sustained revenue and measurable economic impact, not isolated features.
Required Qualifications:
- 7+ years of Product Management experience with direct ownership of analytics, reporting, or intelligence product lines
- Demonstrated experience owning a monetized analytics or intelligence product that generated measurable revenue impact
- Experience supporting enterprise or OEM-level customers with standardized, scalable reporting solutions
- Strong quantitative fluency, including comfort with probabilistic reasoning, forecasting, optimization trade-offs, and economic modeling
- Ability to independently interrogate data using SQL or equivalent tools and translate findings into product direction
- Proven track record of defining economic success metrics and tying product decisions to measurable financial outcomes
- Experience developing pricing and packaging strategies for data-driven products
- Strong executive communication skills with the ability to distill complex data and product strategy into clear, concise presentations for senior leadership and enterprise customers.
Even better if you have:
- Advanced degree in economics, mathematics, engineering, data science, or a similarly rigorous quantitative discipline
- Experience building predictive, optimization, or simulation-based systems in production
- Experience monetizing analytics capabilities in B2B environments
- Experience operating in capital-intensive, asset-heavy, or mobility-related industries
Dealerware offers you:
- Competitive base salary with bonus incentive eligibility
- Full benefits (medical, dental, vision, disability)
- 401(k) with company match
- On-demand educational courses via LinkedIn Learning
- Tuition reimbursement and continuing education
- Unlimited paid vacation policy
- Flexible work
- Generous Paid Parental Leave program
- Modern office and a dynamic team in downtown Austin with free parking
- Friendly, small company environment with a progressive culture
Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment.
*We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.
What the Team is Saying
Gabriela
Manager, UX Research & DEI Council Co-Chair
Matt
CEO
Peter
DevOps Engineer III
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The Company
What We Do
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. By combining a mobile-first approach with fresh design thinking, Dealerware’s industry-leading SaaS platform enables best-in-class fleet management and mobility services for the top automotive dealerships and manufacturers.
Why Work With Us
“I can't speak highly enough of my teammates. We do a great job of hiring curious, smart, dedicated, passionate and friendly people. This is our superpower.” This is a real comment from our engagement survey about our greatest asset and the best reason to work here: our team.
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Dealerware Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
To support operational effectiveness, team collaboration, and company culture, we require all hybrid employees to work onsite in the Austin, TX office at least two days per week on Tuesdays and Thursdays.
Typical time on-site:
2 days a week
Austin, TX
Team members are offered a seat and a warm welcome in our collaborative headquarters in the heart of downtown Austin, TX, whenever it suits their workday needs or preferences.
