Head of Insurance Programs — Remote, Equity

Outdoorsy; Austin (TX); On-site; USD 220,000 - 235,000; Full time

Benefits offered by this job

Company-paid medical premiums

401(k) match

Flexible PTO

Catered lunches

Happy hours

Team-building events

Marketplace discounts

Job summary

Roamly, the Roamly Insurance Platform behind Outdoorsy and related brands, seeks a Head of Insurance Programs to own and optimize a portfolio of mobility insurance programs end to end. You will shape appetite, rate strategy, and carrier relationships while guiding underwriting, actuarial, and compliance functions.

You will collaborate with Sales, Claims, Legal, Product, and Engineering, applying AI/automation to underwriting workflows and portfolio monitoring.

Qualifications

• Lead underwriting guidelines and risk selection across all programs.
• Oversee day-to-day underwriting referrals and decisions.
• Oversee actuarial pricing efforts and rate adequacy decisions.
• Ensure programs comply with regulatory and carrier requirements.

Responsibilities

• Own performance of Roamly's in-market programs, including loss ratio and premium growth.
• Establish KPI framework and run monthly/ quarterly reviews.
• Diagnose adverse trends and implement corrective actions.
• Represent the program portfolio to executives, carriers, and reinsurers.

Skills

Underwriting guidelines

Risk assessment

Portfolio management

Pricing strategy

Regulatory compliance

Cross-functional collaboration

Executive communication

Job description

Roamly, the Roamly Insurance Platform behind Outdoorsy and related brands, seeks a Head of Insurance Programs to own and optimize a portfolio of mobility insurance programs end to end. You will shape appetite, rate strategy, and carrier relationships while guiding underwriting, actuarial, and compliance functions.

You will collaborate with Sales, Claims, Legal, Product, and Engineering, applying AI/automation to underwriting workflows and portfolio monitoring.