Outdoorsy

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, the enterprise SaaS to manage, and the insurtech 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 roamly.com.
About The Role
Reporting to the Head of Insurance Programs, the
Actuary
is the analytical engine behind Roamly's program portfolio. You will build and maintain the pricing, reserving, and performance analysis that tells us how each program is actually doing — and you'll be in the room when those numbers turn into decisions about rate, appetite, and whether a new program gets built.
This is a high-visibility seat at a rapidly growing company.
You won't be handed a narrow slice of a large actuarial department's workflow. You'll touch loss cost modeling, rate indications, reserve reviews, carrier and reinsurance submissions, filing support, and the reporting that goes to executive leadership and carrier partners. When we launch a new program, you'll help build the rating structure from scratch and then watch it earn out in real time.
You'll work across P&amp;C auto, carshare and rideshare, RV, and adjacent mobility lines, and you'll partner closely with Underwriting, Claims, Finance, Product, and Engineering.
We also expect you to bring modern tooling to the work — automating recurring analyses and applying AI where it genuinely speeds up the cycle, rather than rebuilding the same spreadsheet every quarter.
While a cover letter is not mandatory, for a role as nuanced as this, it might help us better understand your qualifications.
<ul>
<li>Preference will be given to candidates in Austin, TX or San Francisco, CA. There is, however, an opportunity for a remote hire for those who meet 100% of the job criteria</li>
</ul>
Requirements
Key Responsibilities &amp; Deliverables
New Program Development
<ul>
<li>Build initial rating structures and pricing models for new programs, including where internal data is thin and external benchmarks or judgment are required</li>
<li>Model program economics — expected loss ratio, commission structure, fronting costs, and profitability under different scenarios</li>
<li>Support implementation by validating rating logic in production systems before launch</li>
</ul>
Program Performance Reporting
<ul>
<li>Produce the recurring loss ratio, frequency, severity, and trend reporting that drives monthly and quarterly program reviews</li>
<li>Build and maintain dashboards that give Underwriting and leadership a current view of portfolio performance without waiting on a request</li>
<li>Investigate emerging trends and adverse development, and translate findings into a clear recommendation rather than a chart</li>
</ul>
Carrier &amp; Reinsurance Support
<ul>
<li>Prepare the loss data, exhibits, and experience analysis that go into carrier submissions, renewal proposals, and reinsurance placements</li>
<li>Support bordereaux accuracy, delegated authority reporting, and carrier audit requests</li>
</ul>
Pricing &amp; Rate Analysis
<ul>
<li>Build and maintain rate indications, loss cost models, and rate level analyses across the program portfolio</li>
<li>Support segmentation and risk selection analysis; identify which segments are performing, which aren't, and what the rate response should be</li>
<li>Perform competitive and market analysis to test pricing adequacy and positioning</li>
<li>Prepare rate, rule, and form filing exhibits and supporting actuarial materials; respond to regulator objections</li>
</ul>
Underwriting Partnership
<ul>
<li>Provide analytical support on underwriting referrals, account-level pricing questions, and appetite decisions</li>
<li>Help maintain and refine underwriting guidelines with data behind the thresholds</li>
</ul>
Who You Are
<ul>
<li>ACAS, FCAS, or equivalent experience</li>
<li>4+ years of P&amp;C actuarial experience, ideally in personal or commercial auto, specialty, or program business</li>
<li>Strong technical foundation in ratemaking, loss reserving, and trend analysis</li>
<li>Advanced Excel skills plus working proficiency in SQL and at least one of Python or R</li>
<li>Experience building reports or dashboards in a BI tool (Tableau, Looker, Power BI, or similar)</li>
<li>Comfortable working with imperfect, incomplete, or newly created data — and honest about the resulting uncertainty</li>
<li>Able to explain an analysis clearly to underwriters, executives, and carrier partners who are not actuaries</li>
<li>Experience with insurtech, MGA, or program business is a plus</li>
<li>Exposure to rate filings and state regulatory processes is a plus</li>
<li>Bachelor's degree in actuarial science, mathematics, statistics, economics, or a related quantitative field</li>
</ul>
What You'll Bring
<ul>
<li>Genuine curiosity about why a number moved, and the persistence to chase it down</li>
<li>A bias toward automating recurring work instead of repeating it</li>
<li>Strong attention to detail with the judgment to know when precision matters and when speed matters more</li>
<li>Comfort in a fast-paced environment with shifting priorities and limited precedent</li>
<li>A collaborative style — willing to sit with underwriters and claims adjusters to understand the business behind the data</li>
<li>Clear written and verbal communication, including the ability to summarize a complex analysis in a paragraph</li>
</ul>
Benefits
Compensation &amp; Benefits:
<ul>
<li>Competitive Compensation: Base salary of $125,000 to $150,000 DOE</li>
<li>Growth Opportunity: Join a company in its early stages and help build its foundation for success</li>
<li>Equity: Opportunity to earn equity compensation</li>
<li>Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) match, and Flexible PTO</li>
<li>Vibrant Culture: Work at either our Austin, TX, or San Francisco, CA, HQ with catered lunches, happy hours, and team-building events</li>
<li>Work-Life Balance: We offer marketplace discounts and maintain a culture that values the balance between work and adventure</li>
</ul>

Roamly - Actuary

Roamly - Actuary

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