Head of Insurance Programs - Roamly

The Ride Platform • Austin, TX

2d • $220,000 - $235,000 • Hybrid

About The Position

As the Head of Insurance Programs at Roamly, you will own our portfolio of insurance programs end to end including the products and programs already in the market, and the ones we haven't built yet. You will be responsible for how each program performs, for the underwriting and actuarial discipline behind it, and for the carrier and reinsurer relationships that give it capacity. This is a role for someone who can operate at both altitudes. You'll set appetite, guidelines, and rate strategy, present at renewal to carrier partners, and build the business case for the next program, and you'll also sit in the daily flow of underwriting referrals, exceptions, and authority decisions that determine whether a program actually performs the way the model says it should. Our programs span P&C auto, carshare and rideshare, RV, and adjacent mobility lines across multiple jurisdictions, so you'll need real fluency in this space rather than a willingness to learn it. You will partner closely with Sales, Claims, Actuarial, Legal and Compliance, Product, and Engineering, and you'll have the opportunity to apply AI and automation directly to underwriting workflow such as referral triage, risk selection, and portfolio monitoring rather than admiring it from a distance.

Requirements

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

Nice To Haves

• Preference will be given to candidates in Austin, TX or San Francisco, CA.
• Opportunity for a remote hire for those who meet 100% of the job criteria.

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.

Benefits

• Competitive Compensation: Base salary of $220,000 to 235,000 DOE.
• Growth Opportunity: Join a company in its early stages and help build its foundation for success.
• Equity: Opportunity to earn equity compensation.
• Comprehensive Benefits: 100% company-paid medical premiums for employees, 401(k) match, and Flexible PTO.
• Vibrant Culture: Work at our Austin HQ with catered lunches, happy hours, and team-building events.
• Work-Life Balance: We offer marketplace discounts and maintain a culture that values the balance between work and adventure.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed