Head of Insurance Programs & Underwriting Strategy

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

Benefits offered by this job

Equity

Medical premiums

401(k) match

Flexible PTO

Catered lunches

Job summary

The Ride Platform, the parent company of Outdoorsy, Ride, Wheelbase, and Roamly, seeks a Head of Insurance Programs for Roamly. You will own end-to-end insurance programs, including underwriting, actuarial discipline, and carrier relationships across mobility lines.

Role spans P&C auto, carshare, rideshare, and RV, with close collaboration across Sales, Claims, Actuarial, Legal, Compliance, Product, and Engineering. Remote options exist for qualified candidates.

Responsibilities

• Own underwriting guidelines, risk selection criteria, appetite, and authority levels across all programs.
• Oversee day-to-day underwriting referrals and exception decisions, ensuring SLAs and delegated authority.
• Lead portfolio underwriting such as monitor in-force distribution, exposure concentration, and segment-level results.
• 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 timelines.
• Partner on reserving and claims analysis to ensure program results are understood accurately and early.
• Own the performance of Roamly’s in-market programs including loss ratio, combined ratio, premium growth, retention, and mix.
• Establish KPI framework and reporting cadence for each program, and run monthly/quarterly performance reviews.

Job description

The Ride Platform, the parent company of Outdoorsy, Ride, Wheelbase, and Roamly, seeks a Head of Insurance Programs for Roamly. You will own end-to-end insurance programs, including underwriting, actuarial discipline, and carrier relationships across mobility lines.

Role spans P&C auto, carshare, rideshare, and RV, with close collaboration across Sales, Claims, Actuarial, Legal, Compliance, Product, and Engineering. Remote options exist for qualified candidates.