Director, Insurance Programs & Underwriting

Outdoorsy; San Francisco (CA); On-site; USD 220,000 - 235,000; Full time

Benefits offered by this job

Equity opportunity

100% company-paid medical premiums

401(k) match

Flexible PTO

HQ Austin with team events

Job summary

Outdoorsy is seeking a Head of Insurance Programs for Roamly to own end-to-end insurance programs—spanning P&C auto, carshare, rideshare, RV and related mobility lines between jurisdictions. You will lead underwriting guidelines, rate strategy, and carrier relationships to enable scalable coverage.

You will partner with Sales, Claims, Actuarial, Legal and Engineering to apply AI/automation to underwriting workflow and portfolio monitoring, ensuring performance aligns with business goals.

Qualifications

• Own performance metrics and reporting for in-market programs.
• Lead underwriting guidelines and risk selection criteria.
• Oversee pricing, actuarial work, and risk segmentation.

Responsibilities

• Own program performance including loss ratios, premium growth and retention.
• Establish KPI framework and monthly/quarterly reviews for each program.
• Diagnose adverse trends and drive action to improve performance.
• Represent the program portfolio to executives, carriers and reinsurers.
• Ensure compliance with regulatory and carrier requirements across jurisdictions.

Job description

Outdoorsy is seeking a Head of Insurance Programs for Roamly to own end-to-end insurance programs—spanning P&C auto, carshare, rideshare, RV and related mobility lines between jurisdictions. You will lead underwriting guidelines, rate strategy, and carrier relationships to enable scalable coverage.

You will partner with Sales, Claims, Actuarial, Legal and Engineering to apply AI/automation to underwriting workflow and portfolio monitoring, ensuring performance aligns with business goals.