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Salary: USD 220,000 - 235,000 / annual
Roamly, the insurtech arm of The Ride Platform (parent company of Outdoorsy, Ride, and Wheelbase), is seeking a Head of Insurance Programs to own the end-to-end portfolio of specialty insurance products for the modern mobility and marketplace travel economy. This is a strategic leadership role combining high-level portfolio management with hands-on underwriting oversight.
You will own performance across all in-market insurance programs (P&C auto, carshare, rideshare, RV, and adjacent mobility lines) spanning multiple jurisdictions. Responsibilities include setting program strategy, managing carrier and reinsurer relationships, establishing KPI frameworks, and driving quarterly performance reviews. You'll diagnose adverse trends early and implement corrective actions through rate adjustments, appetite changes, or program restructuring.
On the underwriting side, you'll oversee guidelines, risk selection criteria, and authority levels. This includes managing day-to-day referrals and exception decisions, ensuring the team meets service level agreements, and conducting portfolio-level monitoring of exposure concentration and segment results. You'll keep underwriting documentation audit-ready and current.
Actuarial and pricing responsibilities include overseeing portfolio and account-level pricing, loss cost modeling, and risk segmentation. You'll own rate adequacy, lead indication processes, translate analysis into pricing decisions, and drive filing strategy for regulated programs. You'll partner with claims and reserving teams to ensure accurate and early understanding of program results.
This role requires deep fluency in P&C insurance, specialty lines, and the mobility/marketplace economy—not a willingness to learn. You'll partner closely with Sales, Claims, Actuarial, Legal, Compliance, Product, and Engineering teams. There's a strong opportunity to apply AI and automation directly to underwriting workflows including referral triage, risk selection, and portfolio monitoring.
Roamly combines Lloyd's Coverholder status with proprietary AI-first technology, deep carrier partnerships, and embedded distribution to deliver tailored coverage across emerging mobility models.
