Staff Product Manager

Staff Product Manager - Insurance Innovation & Ancillary Products We're seeking a Staff Product Manager who operates comfortably in highly ambiguous problem spaces, owns strategy end-to-end, and drives the delivery of complex and innovative product bets from first principles through to material business impact. Working at the intersection of our core marketplace and Sincera (our insurance company), you'll pioneer new revenue streams while delivering genuine value that enhances every customer journey. As a member of our team, your responsibilities will include: Lead Strategic Innovation: Define, communicate, and continuously refine the product strategy for our insurance and ancillary ecosystem - including making clear investment trade-offs, sequencing bets, and validating which opportunities are worth scaling versus killing early. This includes identifying opportunities to diversify beyond our current offerings into travel protection, subscription models, roadside assistance, and other value-added services aligned with customer needs and business growth objectives. Drive Revenue Growth: Own key business metrics, such as performance of ancillary products, translating insights into actionable product initiatives that deliver measurable commercial impact. Champion Customer-Centricity: Conduct deep customer research and data analysis to uncover unmet needs in the travel protection space, designing solutions that genuinely reduce customer anxiety and enhance their travel experience rather than focusing on short-term revenue. This includes designing and running structured experiments (e.g. fake-door tests, pricing experiments, controlled rollouts) to validate demand, value perception, and risk before full-scale investment. Collaborate Across the Organization: Work closely with Sincera's insurance experts to evaluate regulatory requirements, product feasibility, and risk management while partnering with DiscoverCars.com's commercial, legal, design and engineering teams to bring innovative insurance products from concept to market. Execute with Excellence: Translate complex problem spaces - including regulatory, commercial, and technical constraints - into clear product direction, making high-quality decisions with incomplete information and guiding teams through trade-offs rather than simply delivering predefined requirements. Foster Innovation Culture: Actively mentor and coach other product managers, sharing expertise in ancillary revenue strategies, insurance product development, and data-driven decision making to elevate the entire product organization's capabilities. Embrace Emerging Technologies: Leverage AI, machine learning, and other cutting-edge technologies to personalize insurance offerings, optimize pricing strategies, and create more intelligent customer experiences that drive both satisfaction and profitability. Navigate Complexity: Balance multiple stakeholder requirements across customer needs, regulatory compliance, supplier relationships, and business objectives while maintaining focus on delivering incremental, measurable improvements in a fast-paced environment. You will be a great asset for this role if you have these qualities: Mandatory: Strategic Product Leadership: 8+ years of product management experience, including operating at Senior or Staff level with clear ownership over a complex domain, multiple product bets, and measurable commercial outcomes. Commercial Acumen: Proven ability to identify, validate, and monetize new business opportunities, with experience optimizing key metrics like attach rates, ARPB, and customer lifetime value in growth-oriented companies. You have owned revenue-impacting decisions directly and can clearly articulate what you tried, what worked, what failed, and why. Data-Driven Excellence: Advanced analytical skills, including proficiency with SQL, analytics platforms, and A/B testing methodologies, with the ability to translate complex data insights into actionable product decisions and compelling stakeholder narratives. Customer Empathy: Strong user research and discovery skills, with demonstrated ability to understand customer pain points and translate them into innovative product solutions that drive both satisfaction and business results. Execution Focus: Excellent project management and cross-functional collaboration skills, with experience working in agile environments and managing complex product roadmaps involving multiple engineering, design, and business teams. Communication Leadership: Exceptional written and verbal communication skills, capable of influencing senior stakeholders, aligning cross-functional teams, and clearly articulating complex technical and business concepts to diverse audiences. Regulatory Awareness: Comfort operating in regulated environments, with a demonstrated ability to quickly learn regulatory constraints and work closely with legal, risk, and compliance partners to shape viable product solutions. Product Judgment & Autonomy: Demonstrated ability to operate with minimal direction, challenge assumptions (including leadership’s), and independently drive clarity in ambiguous, high-impact problem spaces. Insurance/Fintech Experience: Background in insurance product development, subscription models, or financial services, with understanding of underwriting, claims processes, and regulatory frameworks. Marketplace Expertise: Experience building ancillary products in two-sided marketplaces or travel platforms, with an understanding of supplier relationships and multi-stakeholder product dynamics. Technical Depth: Comfort with API integrations,