Head of Insurance

About Gig Safe

Gig Safe is a contractor management platform built for gig and last-mile delivery operations. We are building infrastructure for the future of 1099 work that helps companies verify, manage, and pay independent contractors at scale.

Gig Safe is a contractor management platform built for gig and last-mile delivery operations. We are building infrastructure for the future of 1099 work that helps companies verify, manage, and pay independent contractors at scale.

The 1099 economy is the fastest-growing segment of the American workforce, and it's been running on duct tape and spreadsheets. A credentialing gap or an uninsured worker isn't just an HR headache here, it's a liability that can shut down a business.

This is a big problem. A large market. And we're early. Come build with us. For more information, visit

Gig Safe is looking for a Head of Insurance to join our Insurance Operations Team and play a leading role in shaping our professionalized Insurance operations.

Insurance touches everything at Gig Safe - it's the difference between a contractor getting deployed or blocked, and a claim closing clean or turning into a liability. Right now it's split across founders, ops, and outside brokers with no single owner. You'll take the whole thing over. You're building the full insurance focus and setting the standard for how Gig Safe does insurance going forward.

• Design and manage insurance programs, including coverage and policy design, rate and commission structure, renewals. Own program economics and repricing. Work with senior leadership to design and build strategic programs that enable our expansions into new industries.
• Manage carrier, MGA, and broker relationships directly. Negotiate terms, run renewals, and serve as the escalation point for underwriting questions on new partner programs.
• Run the compliance & backoffice footprint: resident and non-resident producer licensing, carrier appointments, surplus lines filings, continuing education, E&O, tooling and training, funds flow, and audit readiness. We prioritize and will measure this role against compliant implementation.
• Oversee claims from intake through resolution, coordinating with our TPA and adjusters on coverage determinations and closing the loop with partners and contractors.
• Own certificate operations, setting the standards for COI issuance and verification, additional insured and endorsement requirements, and accuracy at volume.
• Partner with product and engineering to convert manual insurance workflows into software: quoting, eligibility, certificate validation, and reporting.

• 8+ years of experience
• Embedded Insurance, P&C lines
• Licensed for P&C lines at least in resident state, or willingness to get licensed
• Built and managed programs either for clients or internally
• Managed insurance operations
• Experience in a customer facing capacity
• Strong desire for San Francisco or Austin based

• Experience in the logistics, marketplace and/or gig economy industries
• Management experience (team of 3+)
• Underwriting or actuarial experience

• Medical, dental, and vision for you and dependents
• Unlimited PTO plus company holidays
• Competitive base with performance bonus
• 401(k)
• Meaningful equity
• Paid parental leave

Gig Safe is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other characteristic protected by applicable law.