Underwriting & Actuarial Director

About Us

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 (Outdoorsy, Ride), the enterprise SaaS to manage (Wheelbase), and the insurtech (Roamly) 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.

About Roamly

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 www.roamly.com.

About The Role

As the Director of Underwriting and Actuarial at Roamly, you will lead the underwriting and actuarial functions, playing a critical role in shaping the strategy and execution of our product offerings. You will be responsible for leading our underwriting efforts, overseeing actuarial pricing models, and driving portfolio analytics to optimize risk selection and pricing strategies. In this role, you will collaborate with cross-functional teams, including Sales, Engineering, and Product, to develop and refine our insurance offerings and ensure profitability and sustainability.

This is an opportunity to be a key and pivotal member of the Roamly team, shaping the future of insurtech and driving innovation in underwriting and actuarial practices while leveraging and implementing cutting-edge AI practices to enhance processes and drive efficiency. Success in this role requires a strong analytical mindset, deep expertise in risk assessment, pricing, and actuarial science, as well as a keen ability to work across teams to implement data-driven strategies.

While a cover letter is not mandatory, for a role as nuanced as this, it might help us better understand your qualifications.

Key Responsibilities & Deliverables

• Lead the underwriting strategy for Roamly’s products, ensuring alignment with business objectives and risk appetite.
• Oversee actuarial efforts, including portfolio and account-level pricing, loss cost modeling, and risk segmentation to drive profitability.
• Develop and refine pricing strategies, leveraging actuarial analysis and predictive modeling to optimize risk selection.
• Partner with Sales, Engineering, and Product teams to develop innovative insurance products and solutions in collaboration with carrier partners.
• Establish and maintain underwriting guidelines, risk selection criteria, and pricing models to support profitable growth.
• Engage with carrier partners to align on risk appetite, pricing structures, and product development initiatives.
• Monitor key performance indicators (KPIs) for underwriting performance, profitability, and loss ratios.

Who You Are

• 10 or more years of experience in underwriting, actuarial science, or related insurance fields, with leadership experience preferred.
• Strong actuarial background with expertise in pricing models, loss cost modeling, and risk assessment methodologies.
• Experience in insurtech, digital insurance platforms, or embedded insurance solutions is a plus.
• Demonstrated ability to develop and implement underwriting guidelines and actuarial pricing strategies.
• Strong analytical skills with proficiency in actuarial software and data analysis tools.
• Ability to work cross-functionally and influence decision-making across teams.
• Deep understanding of insurance regulations, compliance, and market dynamics.
• Bachelor's degree in actuarial science, finance, business, or a related field. A designation such as ACAS, FCAS, or CPCU is a plus.

What You'll Bring

• Excellent communication, negotiation, and presentation skills, with the ability to influence and build relationships at all levels of the organization.
• A strategic mindset with a passion for innovation in underwriting and actuarial functions.
• A results-oriented approach with a focus on optimizing risk and profitability.
• Ability to thrive in a fast-paced, dynamic environment and adapt to changing business priorities.
• Strong organizational and time management skills with a detail-oriented mindset.

Compensation & Benefits:

• Competitive Compensation: Base salary of $220,000 to $235,000 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: Catered lunches, happy hours, and team-building events.
• Work-Life Balance: We offer marketplace discounts and maintain a culture that values the balance between work and adventure.