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Head of Product - Roamly

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About Roamly

Roamly Insurance Group (Roamly), a wholly owned subsidiary of Outdoorsy Holdings, Inc., is the first full-stack insurtech with an embedded offering that powers insurance. Our offerings include modern-day RV insurance to make owners' vehicles 'rent ready,' which we dogfood in our Outdoorsy marketplace, and the RAC platform - a suite of unique digital insurance products that eliminate the commercial use exclusion clause prohibiting online renting activity. RAC enables marketplaces to embed and offer a broad array of insurance products – such as rental insurance, trip and travel insurance, and pet insurance, among others – directly to customers through simple booking flows. RAC is a state-of-the-art, never-before-seen platform in the insurance industry that combines predictive analytics AI/ML, cutting-edge actuarial science, proprietary underwriting processes, and proprietary state filing methodologies implemented on an API-first platform. This platform combines location services, informatics, and real-time data. Our solution revolutionizes claims handling and subrogation while mitigating risk in ways industry insiders describe as a revelation. Our insurtech also markets personal and professional insurance products to peer-to-peer and marketplace businesses to complete our end-to-end offering.

At Roamly, we move fast, and our business is growing quickly because of it. Our net written premiums have increased 130% year-on-year, and our growth continues to accelerate. Is half a trillion dollars in net written premiums a big number for you? We believe we’ll get there in just a short number of years at our current rate!

At Outdoorsy Holdings, we are driven by a profound commitment to reconnect people with nature and foster deeper interpersonal connections. 2023 marked a milestone for us as we achieved profitability, and we are currently experiencing a robust multi-year growth rate of 175%. In 2024, we anticipate surpassing $3 billion in transactions. Our success story includes celebrating over 1 million trips and more than 7 million booked travel days as of June 2023. Join us as we disrupt the outdoor travel industry.

About you

You are an enterprising leader in the Insurance sector, celebrated for your extensive experience, notably over 10 years of transformative work in insurtech or fintech, with a focus on product management. Your journey has been marked by managing a diverse range of personal lines, products, and embedded platforms, standing as a testament to your professional prowess. Your approach is that of a builder, infused with the innovative spirit and agility of a startup, skillfully taking projects from concept to market realization, underlined by your decisive action-oriented mindset.

As the newest addition to Roamly Insurance Group, a trailblazer in the insurtech domain and a wholly owned subsidiary of Outdoorsy Holdings, Inc, your role is not just significant; it's revolutionary. You will play a pivotal role in expanding our comprehensive product portfolio, which includes cutting-edge RV insurance and our groundbreaking RAC platform, eliminating traditional commercial use exclusion clauses and integrating advanced AI/ML analytics and state-of-the-art actuarial science.

Your mission involves driving product-led growth across all 50 states and Canada, closely collaborating with co-founders to chart out strategic roadmaps and spearheading market entry for novel product lines. Your acumen will be crucial in harmonizing product changes with our actuarial and underwriting teams, managing loss ratios, and innovating in product performance through robust, data-driven strategies.

In your hands lies the responsibility to enhance our claims experience across multiple products, leveraging Roamly’s API-first platform that synergizes location services, informatics, and real-time data for revolutionary claims handling and risk mitigation. Your digital expertise, analytical proficiency, and exceptional product sense will be the cornerstone in driving Roamly's rapid growth, with our sights set on ambitious targets in net written premiums.

Your passion lies in not just joining but significantly contributing to an early-stage tech-based insurance business. At Roamly, where we move swiftly and our business grows exponentially, your impact will be immediate and profound. You are here to not only witness but actively shape our journey towards an ambitious future in the insurtech industry.

Your work at Roamly

  • Lead Product Development: Spearhead the lifecycle of innovative insurance products, focusing on RV insurance and RAC platform enhancements.
  • Facilitate Team Collaboration: Collaborate with co-founders, actuaries, underwriters, and data scientists to align product vision with company goals.
  • Expand Market Reach: Strategically expand product offerings across all 50 states and Canada, ensuring regulatory compliance.
  • Optimize Products through Data: Utilize AI/ML analytics and actuarial insights for product performance improvement and loss ratio management.
  • Revolutionize Claims Processing: Enhance claims experience by leveraging Roamly’s API-first platform, integrating real-time data for efficient risk mitigation.
  • Engage Stakeholders: Actively engage with investors, regulatory bodies, and customers for product feedback and strategy refinement.
  • Conduct Market Research: Perform market analysis and competitive intelligence to guide product development and positioning.
  • Monitor Performance Metrics: Establish and track key performance indicators for product lines, providing regular reports to senior management.

What you bring to the table

  • Professional Background: At least 10 years in product management within insurtech or fintech, with a focus on managing personal insurance products.
  • Educational Qualifications: Bachelor’s degree in Business, Finance, Insurance, Actuarial Science, or a related field. Advanced degrees or certifications like CPCU, CFA preferred.
  • Technical Proficiency: Skilled in AI/ML analytics, big data, and actuarial practices. Experience with API-first platforms and digital insurance solutions.
  • Regulatory Acumen: Deep understanding of insurance regulations in various jurisdictions, including U.S. states and Canada.
  • Leadership Capabilities: Proven leadership and team management abilities, with a track record of motivating cross-functional teams.
  • Strategic Aptitude: Strong strategic thinking and analytical skills, adept at market opportunity identification and product strategy development.
  • Communication Skills: Excellent communication abilities for effective stakeholder engagement and complex concept articulation.
  • Adaptability: Ability to thrive in a dynamic, fast-paced environment and adapt to changing business needs.
  • Innovation-Driven: Passion for contributing to a tech-forward, early-stage company in the insurtech sector.

  • 401K
  • Discretionary PTO
  • Health, vision, and dental insurance
  • Equity in the company
  • However, the compensation package is usually the second reason people choose to join a startup. The primary reason is they want to experience the growth that comes from pouring your heart and soul into building something people love and winning a market. That's what we do at Roamly.

Salary: $150,000 - $225,000 DOE

The expected compensation range for this position is displayed in accordance with potentially applicable laws. The final agreed-upon compensation is based on a number of factors, including but not limited to: individual education, qualifications, prior work experience, and geographic work location. The total annual compensation package may consist of a base salary and bonus dependent upon position.

It is the policy of Outdoorsy Holdings, Inc. to provide equal employment opportunities without regard to race, color, religion, sex, national origin, age, disability, marital status, veteran status, sexual orientation, genetic information or any other protected characteristic under applicable law. This policy relates to all phases of employment, including, but not limited to, recruiting, employment, placement, promotion, transfer, demotion, reduction of workforce and termination, rates of pay or other forms of compensation, selection for training, the use of all facilities, and participation in all company-sponsored employee activities.

We continue to have our home and headquarters in Austin, Texas, but we have embraced a distributed model of working to reach the best talent in the United States and globally. While some roles may require proximity to our Austin office, roles based outside of our Austin office can sit in any of the following 21 US states: AR, AZ, CA, CO, FL, GA, IL, IN, MN, MO, MT, NV, OH, OK, SD, TN, TX, UT, VA, WA and WV. Please only apply if you are able to live and work full-time in one of the states listed above. State locations and specifics are subject to change as our hiring requirements shift.