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About the Role

As the Head of Insurance Programs at Roamly, you will own our portfolio of insurance programs end to end, including current and future products. You will be responsible for program performance, underwriting and actuarial discipline, and managing carrier and reinsurer relationships. This role requires operating at both strategic and tactical levels, setting appetite, guidelines, and rate strategy, while also managing daily underwriting referrals and decisions. Fluency in P&C auto, carshare, rideshare, RV, and adjacent mobility lines across multiple jurisdictions is essential. You will partner closely with Sales, Claims, Actuarial, Legal and Compliance, Product, and Engineering, with opportunities to apply AI and automation to underwriting workflow.

Responsibilities

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.
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.
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.

Requirements

Real fluency in P&C auto, carshare and rideshare, RV, and adjacent mobility lines across multiple jurisdictions.

Skills

AI and automation applied to underwriting workflow such as referral triage, risk selection, and portfolio monitoring.

Location

Austin, TX
San Francisco, CA
Remote

Work Type

Remote

Experience Level

Salary/Compensations

$220,000 to $235,000

Benefits

100% company-paid medical premiums for employees
401(k) match
Flexible PTO
Marketplace discounts

About the Company

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.
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.