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About GigSafe
GigSafe 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 gigsafe.com
About the Opportunity
GigSafe 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 GigSafe – 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 GigSafe does insurance going forward.
Responsibilities
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.
Qualifications
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
Preferred
Experience in the logistics, marketplace and/or gig economy industries
Management experience (team of 3+)
Underwriting or actuarial experience
Benefits
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
GigSafe 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.
Skills Required
- 8+ years of professional experience
- Experience with embedded insurance and property and casualty lines
- P&C licensing in the resident state or willingness to obtain licensing
- Experience building and managing insurance programs for clients or internally
- Experience managing insurance operations
- Experience in a customer-facing capacity
- Strong preference for candidates based in San Francisco or Austin
- Experience in logistics, marketplace, or gig economy industries
- Management experience leading a team of three or more
- Underwriting or actuarial experience
What We Do
GigSafe gives companies the tools they need to onboard, pay, and stay on top of compliance for their independent contractor (IC) network—all in one place. We work with gig platforms, delivery services, home-service companies, staffing groups, dispatch operations, and any business that depends on a distributed 1099 workforce. Most teams today are stuck juggling a mess of systems: one tool for onboarding, another for compliance, another for payments, another for insurance—and endless spreadsheets in between. It’s slow, manual, and easy for things to fall through the cracks. Contractors feel it too: confusing requirements, repeated paperwork, and delays that keep them from getting to work. GigSafe brings everything together in one simple platform. We automate onboarding, collect and verify documents, keep an eye on ongoing compliance, and sync data wherever it needs to go. We also streamline payments and consolidate reporting so companies always know exactly where things stand with every contractor. Insurance is part of the picture, but it isn’t the whole story. Our platform helps companies track coverage, manage certificates, and meet requirements automatically—without chasing paperwork or relying on manual checks. For contractors, that means a cleaner, clearer experience that gets them up and running faster. Our goal is to make it easier for companies and contractors to work together. By removing busywork and operational friction, we help teams move faster, stay compliant, and operate with confidence—all while giving contractors a more modern and transparent experience. In short: GigSafe gives companies one place to manage onboarding, compliance, payments, insurance, and day-to-day operations for their entire IC network.
Why Work With Us
GigSafe is a small, fast-moving team building tools that make work easier for companies and the contractors they rely on. We live our values—do right by customers, find ground truth, give a shit, build through it—and we want people who care, take ownership, and want to make an immediate impact.
