Thimble Insurance:
An Honest Review

Thimble was founded in 2015 in New York as Verifly — an on-demand drone insurance company that let pilots buy coverage by the hour. The company rebranded as Thimble in 2019 and expanded its on-demand model to the broader small business insurance market. Today Thimble covers 300+ professions with GL, BOP, professional liability, workers' comp, cyber, and commercial property policies that can be purchased by the job, by the month, or by the year. Coverage is underwritten by Markel Insurance Company, rated A- Excellent by AM Best. Thimble is backed by Liberty Mutual's venture arm among other investors.

Thimble's innovation is the coverage duration model. Traditional business insurance is annual. Thimble recognized that millions of gig workers, freelancers, photographers, and project-based contractors don't need — and can't afford — year-round annual policies for work they do occasionally. A wedding photographer who shoots 20 events a year doesn't need 365 days of GL coverage. A handyman who takes on occasional weekend jobs doesn't need a full commercial BOP. Thimble's by-the-job model lets these workers get coverage exactly when they need it — for a day, a week, or a project — and skip it when they don't.

Options Insurance began placing clients with Thimble in 2024. The use case is specific and clear: gig workers, project-based contractors, and anyone who needs short-term coverage for a single job or event. For established businesses needing year-round coverage, Thimble is not the right tool. But when the niche applies — a photographer who needs a COI for a venue, a contractor who needs one-time coverage for a specific project — Thimble is often the only practical answer in the market.