Head Of Insurtech Jobs (NOW HIRING)

The Ride Platform Inc. is the parent company of Outdoorsy, Ride, Wheelbase, and Roamly. We're named for the thing every part of our business runs on: the ride — the single transaction where an operator meets a renter. We're the only company building end-to-end for the Operator Economy: the marketplaces to book, the enterprise SaaS to manage, and the insurtech to protect the assets people turn into profitable businesses. We enable millions of people to explore the world while helping independent operators build generational wealth. Our mission is to build the essential infrastructure for the mobility economy.

Roamly is a leading provider of specialty insurance for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, we combine deep carrier partnerships with proprietary technology to help consumers, professional fleet owners, and marketplaces unlock new revenue while managing risk. Our platform uses AI, automation, and embedded distribution to deliver tailored coverage for RVs, carsharing, and other emerging mobility models — spanning underwriting, claims, compliance, analytics, and real-time risk management. Learn more at roamly.com.

As a Senior Product Manager at Roamly, you will be the engine of execution for our diverse consumer portfolio, including RV insurance, Carsharing, and F&I protections. This role is built for a high-initiative "full-stack" operator who thrives in the intersection of technical distribution, operational excellence, and modern AI tools. You aren't just managing features; you are owning the complete end-to-end delivery of products that protect our community of adventurers.

Working closely with the Head of Product, you will operate as a metrics-driven problem solver with a deep "MVP mindset"—moving fast, testing, and iterating to navigate ambiguity. You will lead the charge in optimizing our multi-channel distribution while leveraging advanced AI capabilities to unblock engineering, conceptualize high-quality designs, remove operational dependencies, and drive rapid execution.

• Own the product development lifecycle from requirement definition through launch and post-production iteration, seamlessly integrating AI tools into daily workflows.
• Establish clear business objectives and success metrics, then leverage AI tools (e.g., Claude, Gemini) to translate goals into actionable prompt executions and detailed specifications.
• Demonstrate strong product taste by utilizing AI design and prototyping tools to autonomously conceptualize intuitive, high-quality user experiences (UX/UI) and generate production-ready wireframes.
• Accelerate engineering delivery by utilizing AI coding tools (e.g., Claude Code, Cursor) to generate execution code. Act autonomously to unblock velocity by either submitting code changes directly to the repository or conducting efficient technical handoffs to the Engineering team.
• Own the Roamly product backlog, collaborating closely with Engineering and Design to ensure continuous progress and high-quality delivery.
• Lead QA/UAT testing, manage defect resolution, and partner with Engineering to develop creative technical workarounds for system constraints.
• Execute high-velocity, data-driven iterations utilizing a "test and learn" methodology to optimize features and distribution strategies.
• Drive change management, author release notes, and conduct user training for Sales and Service teams to ensure successful product adoption.

• Support the Head of Product in developing the knowledge base and Standard Operating Procedures (SOPs) for our AI Agents and virtual assistants.
• Optimize the Quote-to-Bind experience across several distribution channels: Digital, AI Agent, Embedded, Captive Agency, and Independent Agents.
• Enhance the Customer Portal to improve self-service capabilities and overall policyholder satisfaction.
• Drive operational efficiency for a growing customer base by identifying pain points and supporting system workflows across the Policy Management System (PMS), Close.io, and Zendesk in partnership with Sales, Service, and Claims.
• Optimize our billing and payment systems to deliver a seamless, best-in-class consumer billing experience while maintaining tight, compliant payment workflows that ensure operational efficiency and accurate revenue collection.
• Autonomously manage external partners and vendors, facilitating technical integrations and ensuring successful, long-term partnerships with minimal oversight.
• Support Product Marketing by creating product fact sheets, personas, and value propositions for new and existing products.
• Collaborate with Legal to ensure all products and features remain compliant with state insurance regulations.

• Insurance Expert: 5–8 years of insurance experience. Deep knowledge of the Property & Casualty (P&C) insurance industry is required.
• Industry Background: Previous experience working within insurance carriers, MGAs, or Insurtechs.
• Product Driver: Experience in digital product management with a proven track record of taking defined products through a successful launch. You possess strong product taste and an innate sense for excellent UX/UI.
• AI-Forward Operator: You have integrated AI tools (e.g., Claude, Gemini, Cursor) into your daily product management workflow as a force multiplier rather than just a personal productivity tool. You are inherently curious, continuously developing your AI skill set, and comfortable leaning on these technologies to generate specifications, execution code, and design concepts. Crucially, you possess the critical eye to evaluate AI-generated outputs, filter out substandard or hallucinated content, and consistently ensure high-quality, production-ready deliverables.
• Velocity-Focused: You thrive in fast-paced environments where priorities shift quickly and you're energized by solving real customer problems.
• Collaborative Team Player: You work effectively across departments and understand that great products come from diverse perspectives.
• Academic Background: Bachelor's degree in Business, Finance, Computer Science, or a related field.

• Mobile App Experience: Proven experience building and launching consumer-facing mobile applications (iOS/Android).
• Data & Analytics: Comfortable with product analytics in general and capable of making data-driven decisions. Experience with tools like Amplitude, Mixpanel, or Tableau is a plus.
• Design & Workflow: Familiarity with design tools (such as Figma) and proficiency with standard PM software (JIRA, Confluence).

• Competitive Compensation: Base salary of $150,000 to $175,000 DOE.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) match, and Flexible PTO.
• Work-Life Balance: We offer marketplace discounts and maintain a culture that values the balance between work and adventure.