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Director - Underwriting & Actuarial

OutdoorsyOnsite

Description


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


Requirements


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


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

Life at Outdoorsy

Outdoorsy is largest and most trusted RV rental experiences marketplace on the planet. Powering road trips and RV adventures. At Outdoorsy, we're on a mission: We believe everyone should have the access, choice and opportunity to get outdoors. We don't own a fleet of identical, anonymous RVs that have seen millions of miles. We're a peer-to-peer marketplace, mobilizing the 18+ million underutilized, idle RVs around the world, ensuring everyone has the access, choice and opportunity to safely enjoy outdoor recreational vehicle travel and empowering RV owners to realize financial benefits. For RV Owners: We turn their recreational vehicles into profitable businesses by giving them the necessary tools - access to capital, marketing resources, insurance and customers. For Renters: We provide access to the greatest selection of recreational vehicles and more choices than ever before to rent stylish awesome RVs. Our selection spans vintage Airstreams, toy haulers, fifth wheelers, Class A, B, and C of RV, as well as garden variety trailers and motorhomes. Outdoorsy is safe, easy, fully insured, and has a great local selection. We're free to join and have no membership fees of any kind. Discover amazing RVs to travel in - or rent out your own! Come along for the ride with us here: https://www.outdoorsy.com/blog https://www.facebook.com/GoOutdoorsy/ https://plus.google.com/+OutdoorsyCoRV https://www.pinterest.com/GoOutdoorsy/eq=outdoorsy.&etslf=6234 https://twitter.com/Outdoorsy https://www.instagram.com/outdoorsy/ Tag #Outdoorsy and #NeverIdle to share your stories
Thrive Here & What We Value1. Emphasis on personal and professional growth2. Competitive salary and equity in one of the world's fastest-growing companies3. Comprehensive health and welfare benefits4. Opportunity to help build a company from an early stage5. Distributed model of working to reach the best talent globally
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