Senior Product Manager

About the Outdoorsy Group

Founded in 2015, Outdoorsy Group pioneered access to the outdoors by building the world’s leading outdoor travel ecosystem. Millions of guests trust Outdoorsy to create lifelong family memories, while hosts rely on its products and innovations to grow their businesses and unlock life-changing sources of income. Outdoorsy Group’s portfolio includes Outdoorsy.com, the largest outdoor travel and hospitality marketplace; the Destination Network, a growing collection of campgrounds and glamping retreats set in some of the country’s most iconic landscapes; and Roamly, its proprietary insurtech platform powering Outdoorsy.com and enabling insurance infrastructure for global marketplaces. Together, Outdoorsy Group’s businesses are united by a long-term mission: to restore our relationship with the outdoors—and with one another.

About Roamly

Roamly is a leading provider of innovative, specialty insurance solutions purpose-built for the modern mobility and marketplace travel economy. As a Lloyd's Coverholder and AI-first insurance innovator, Roamly delivers a robust platform, deep carrier partnerships, and an expanding ecosystem that empowers consumers, professional fleet owners, and marketplaces to unlock new revenue streams while reducing risk. Our technology harnesses AI, advanced automation, and embedded distribution to power tailored coverages for recreational vehicles, carsharing, and other emerging mobility models—covering everything from underwriting and claims to compliance, data analytics, and real-time risk management. Learn more at www.roamly.com.

About the Role

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 and operational excellence. 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. With a blend of autonomous ownership and feature-specific leadership, you will lead the charge in optimizing our multi-channel distribution while leveraging cutting-edge AI tools to drive efficiency and growth.

*Candidates in Austin, TX will be prioritized.

Requirements

Key Responsibilities & Deliverables

Product Execution & High-Velocity Delivery:

• Drive the product development lifecycle from requirement definition through launch and post-production iteration.
• Write clear and complete PRDs and user stories to effectively translate business objectives into development priorities.
• Own the Roamly backlog, collaborating daily with Engineering (ENG) and Design to maintain progress and ensure quality delivery.
• Support product quality by conducting QA/UAT testing, managing defect resolution, and troubleshooting system issues with ENG to develop creative workarounds.
• Execute high-velocity iterations by applying a "test and learn" approach to enhance existing features and distribution strategies.
• Support change management and rollouts, including writing release notes and conducting user training for Sales and Service teams.

Operational Scope:

• 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.
• 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.
• Leverage AI tools (e.g., Gemini, Claude) for day-to-day productivity, rapid prototyping, market research, and analyzing customer feedback to identify business opportunities and inform prioritization.

Who You Are (Candidate Profile)

Required Qualifications:

• 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 is strongly preferred.
• Product Driver: Experience in digital product management with a proven track record of taking defined products through a successful launch.
• 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.

Preferred Skills:

• AI Proficiency: Experience leveraging tools like Gemini or Claude for productivity and prototyping.
• Data & Analytics: Proficiency with Tableau and experience with analytics tools like Mixpanel.
• Design & Tooling: Familiarity with Figma and proficiency with standard PM software (JIRA, Confluence, G-Suite).

Benefits

Why You'll Love Working Here

• Competitive Compensation: Base salary of $140,000–$172,000 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.
• Vibrant Culture: Lively Austin HQ with catered lunches, Happy Hours, and team-building events.
• Work-Life Balance: Enjoy RV rental discounts and a company culture that values a healthy balance between work and adventure.