Head of Insurance Programs - Roamly

About Us The Ride Platform 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. About The Role As the Head of Insurance Programs at Roamly, you will own our portfolio of insurance programs end to end including the products and programs already in the market, and the ones we haven't built yet. You will be responsible for how each program performs, for the underwriting and actuarial discipline behind it, and for the carrier and reinsurer relationships that give it capacity. This is a role for someone who can operate at both altitudes. You'll set appetite, guidelines, and rate strategy, present at renewal to carrier partners, and build the business case for the next program, and you'll also sit in the daily flow of underwriting referrals, exceptions, and authority decisions that determine whether a program actually performs the way the model says it should. Our programs span P&C auto, carshare and rideshare, RV, and adjacent mobility lines across multiple jurisdictions, so you'll need real fluency in this space rather than a willingness to learn it. You will partner closely with Sales, Claims, Actuarial, Legal and Compliance, Product, and Engineering, and you'll have the opportunity to apply AI and automation directly to underwriting workflow such as referral triage, risk selection, and portfolio monitoring rather than admiring it from a distance. While a cover letter is not mandatory, for a role as nuanced as this, it might help us better understand your qualifications. Program Performance Own the performance of Roamly's in-market programs including loss ratio, combined ratio, premium growth, retention, and mix. Establish the KPI framework and reporting cadence for each program, and run the monthly and quarterly performance reviews. Diagnose adverse trends early and drive corrective action, whether that's rate, appetite, guideline changes, or restructuring the program itself. Represent the program portfolio to executive leadership, carrier partners, and reinsurers. Ensure programs operate within regulatory, contractual, and carrier requirements across the jurisdictions we write. Underwriting Own underwriting guidelines, risk selection criteria, appetite, and authority levels across all programs. Oversee day-to-day underwriting referrals and exception decisions, ensuring the team clears within service level agreements and within delegated authority. Lead portfolio underwriting such as monitor in-force distribution, exposure concentration, and segment-level results, and adjust before performance deteriorates. Keep guidelines, referral thresholds, and underwriting documentation current, audit-ready, and actually used. Actuarial & Pricing Oversee actuarial efforts including portfolio and account-level pricing, loss cost modeling, and risk segmentation. Own rate adequacy: lead the indication process, translate analysis into pricing and appetite decisions, and drive filing strategy and implementation timelines for filed programs. Partner on reserving and claims analysis to ensure program results are understood accurately and early. 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.