Director - Underwriting & Actuarial

About Roamly

Roamly Insurance Group (Roamly), a wholly owned subsidiary of Outdoorsy Holdings, Inc, is the first full stack insurtech for travel enthusiasts with an embedded offering that brings modern-day RV insurance to make owners' vehicles 'rent ready.' Roamly provides a suite of unique digital insurance products that eliminate the commercial use exclusion clause that prohibits online renting activity. Roamly enables marketplaces to embed and offer a broad array of insurance products – such as rental insurance, trip and travel insurance, and pet insurance, among other offerings – directly to customers through simple booking flows. Additionally, the insurtech markets personal and professional insurance products to peer-to-peer and marketplace businesses. For more information, visit 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.

*We are prioritizing candidates who currently live in or are willing to relocate to the Austin, TX Metro area to work from our office. While we are focusing on local talent,  on rare occasion we may consider exceptional candidates from other locations.

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

Your Work at Roamly:

• 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.

To help us level up, you'll ideally have:

• 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.

To be successful, 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.

Benefits & Perks:

• Opportunity to help build a company from an early stage
• Competitive salary
• Equity in one of the world's fastest-growing companies
• Comprehensive health and welfare benefits
• 401(k) Match
• Flexible PTO