An afternoon’s work can come with a peculiar admission price: a year’s insurance. For someone photographing an event or testing a weekend business, that is an awkward bargain. Thimble’s founding insight was to change the size of the purchase. Give people a way to insure the job they have, and they might be able to accept it.
- Buy eligible coverage by the job, month or year.
- Get proof of insurance without a prolonged paperwork chase.
- Compare durations carefully: frequent work can favor an annual policy.
Insurance is often described as protection against a future catastrophe. For a small operator, it can also be the thing a client demands before tomorrow’s work begins. Thimble occupies that moment between an opportunity and permission to take it. Its audience includes contractors, landscapers, photographers, makers and event professionals, people whose businesses can be substantial without being large.
The customers looked down from the sky
The first product had a much narrower horizon. In 2016, the founders, Jay Bregman and Eugene Hertz, launched Verifly’s on-demand liability insurance for commercial drone pilots. A flight was a useful unit of work: bounded, identifiable, short. According to Thimble’s history, Verifly sold more than 35,000 policies in less than two years.
Then pilots asked about their other jobs. Could the same service cover photography? Construction? Painting? DJ work? The customer, it turned out, had more occupations than the product had imagined. Those requests pushed the company toward broader business coverage. The interesting lesson is that a narrow starting market can teach a company about a much wider buying problem.
In October 2019, Verifly became Thimble and announced a $22 million Series A led by IAC. The name could accommodate a gardener as comfortably as a drone pilot. The original offering did not remain forever: Thimble now says the Verifly app no longer provides drone coverage. Past policy records remain accessible. Expansion and retirement can belong to the same company history.
Forty-five people. Two days. $464.60.
To see the proposition at work, consider Thimble’s own advertising production. In a February 2022 account, the company described a two-day photo and video shoot with 45 crew members. Executive producer Sean Barth booked a policy with a $1 million limit and added the studio as an additional insured. The reported premium was $464.60.
This is a company account, and one production’s premium cannot price another. But it supplies something insurance marketing often lacks: a specific purchase with a specific duration. Thimble also publishes median general-liability premiums by time period. Those figures illustrate the entry point; location, occupation, limits and other details affect an actual quote.
The arithmetic invites a useful question. At the published medians, four daily purchases total $60, against $49 for a month. These are different customer samples, so that is no guaranteed saving. It is a reason to compare quotes once the diary fills up. Flexibility has value, but repeatedly buying the smallest package may cost more.
The certificate is part of the product
Thimble arranges several kinds of protection. General liability addresses covered claims involving third-party injury or property damage. Professional liability addresses covered financial losses arising from professional services. Equipment protection concerns the tools used for work. A business owners policy combines general liability with commercial property coverage. Workers’ compensation serves a separate purpose: workplace injury and illness.
The distinctions matter. A camera, an injured client and a disputed deliverable are different problems. A fast checkout does not make their policies interchangeable. Thimble’s expertise lies in packaging commercial coverage and administering it digitally, with carrier partners supplying the insurance behind the interface.
“Candle maker! They acknowledged me!”Tina Renee W. · customer testimonial published by Thimble
There is another customer on the other side of the certificate: the person hiring the contractor. Thimble’s free Certificate Manager lets that person request documents, compare them with requirements and track expirations. Vendors can buy coverage through the system. Thimble explains the economics plainly: the tool is free because the company sells insurance. Paperwork creates a distribution opportunity.
The small policy meets the large insurer
Thimble is an insurance producer, described in its latest announcement as a digital MGA. It works with insurers including Markel and National Specialty. Customers pay premiums; participating licensed producers receive commissions on collected premiums. The website, app and broker portal provide routes to the same broad task: getting an eligible business insured.
Digital convenience has competitors. ERGO NEXT and Hiscox also offer online small-business coverage. Thimble’s more distinctive proposition is the combination of short durations, ongoing policies and certificate tools. Its own producer guidance says annual insurance is usually the most economical option for continuing operations. The business can follow customers as their occasional work becomes regular work.
Arch Insurance acquired Thimble in April 2023, announcing that existing carrier partnerships would continue. In July 2025, Ian Westerman became President, succeeding Bregman. In September 2026, Thimble announced a Bold Penguin integration using AI agents to support quoting and binding within brokers’ workflows. The original effort to reduce the wait now extends to the intermediaries.
Buy the right stretch of time
The practical lesson is to match the commitment to the work. Compare on-demand, monthly and annual quotes using the same activity, limits and required endorsements. Check that the client’s requirements match the policy. Availability varies by state and insurer, and a business owners policy is annual rather than an hourly purchase.
Short coverage makes less sense when operations continue between booked jobs, contracts require uninterrupted insurance or the work falls outside an insurer’s accepted activities. The calendar is only part of the decision. Thimble’s enduring idea is nevertheless useful well beyond insurance: make the first purchase small enough for a customer to begin, then offer a sensible next purchase when the work grows.