Thimble business insurance

Overview

Thimble is an insurance agency, not an insurance company. Its help center puts it plainly: Thimble is an insurance producer that connects you to a policy, and the policy is provided by its carrier partners. The licensed entity is Verifly Insurance Services, LLC, doing business as Thimble Insurance Services, a New York company regulated by the New York State Department of Financial Services (producer license 1417833), with producer licenses in every state and the District of Columbia.

Who issues the policy depends on what you buy. Thimble's general liability is underwritten by Markel Insurance Company (NAIC 38970) and National Specialty Insurance Company (NAIC 22608), both part of the Markel group. Business owner's policies come through Coterie, with policies issued by Benchmark Insurance Company or Spinnaker Insurance Company, and workers' compensation comes through EMPLOYERS and its Cerity brand (see EMPLOYERS). Drone liability, still sold under the Verifly name, is placed with Global Aerospace, which manages an underwriting pool.

Since April 2023 Thimble has been owned by Arch Insurance, the specialty insurer within Arch Capital Group. Arch said at the time that Thimble would keep growing with its existing carrier partners, including Markel and EMPLOYERS, and its help center in 2026 still names those carriers rather than Arch. Thimble is paid like any agency: its producer compensation disclosure says it is paid by the insurer, or another third party, based on the policy sold, and that the volume or profitability of business it sends an insurer may also affect what it earns. You can ask for details on any placement.

History

Thimble began as Verifly, which launched in 2016 with on-demand, per-flight liability insurance for commercial drone pilots and says it sold more than 35,000 policies in under two years. Customers asked for the same kind of coverage for their other work, so Verifly added general liability by the hour for photographers, handymen, painters and DJs. In October 2019 it rebranded as Thimble and announced a $22 million Series A led by IAC; founder Jay Bregman, who earlier founded the ride-hailing company Hailo, was CEO. By then it covered more than 100 professions.

Arch Insurance announced on April 10, 2023 that it had acquired Thimble, which had sold more than 170,000 policies to small businesses since May 2018. Terms were not disclosed. Thimble has since added a BOP through Coterie, workers' comp through EMPLOYERS, monthly and annual policy terms, a broker program for independent agents, and, in July 2026, higher general liability limit options.

Business insurance products

General liability is the core product. It is an occurrence form built on ISO CG 00 01 (04 13 edition) with Thimble's own endorsements and exclusions. You choose how long you need it:

• On Demand: by the hour, day or job, paid upfront. The minimum premium is $5.
• Thimble Monthly: rolls over each month and is charged three days before renewal; it can be paused.
• Annual: a traditional 12-month policy.

As of July 2026 the limit options are $1 million per occurrence with a $1 million or $2 million aggregate, and $2 million per occurrence with a $2 million or $4 million aggregate. The $2 million/$4 million option is not offered in California or in parts of Connecticut, Florida, Illinois, New Jersey, New York and Pennsylvania (Philadelphia). There is no deductible. The policy is primary and noncontributory by endorsement, carries $5,000 of medical payments, applies anywhere in the U.S., its territories and Canada, and lets you add additional insureds at no charge. It does not cover injury to you or your crew (that is workers' comp territory), damage to vehicles in your care, or cyber. Applicants need less than $15,000 of losses in the past three years.

Other lines:

• Professional liability for consultants and freelancers, including IT consultants, designers, web developers, writers, notaries and photographers, in fewer states than GL.
• Business owner's policy for businesses with no more than 50 employees and $10 million in revenue. Building coverage is only for premises the business owns. See What is a business owner's policy (BOP)?.
• Workers' compensation through EMPLOYERS, with the usual year-end premium audit.
• Business equipment protection with $1,000, $2,500 or $5,000 limits and a $500 deductible, paid on an actual cash value basis, available only with a Thimble Monthly policy.
• Customer property coverage, special event liability (weddings, business events, concerts, recreational sports) and drone liability.

Thimble does not sell commercial auto.

Who it insures

Independent workers and very small businesses: handymen, cleaners and janitors, beauty and fitness professionals, pet sitters and groomers, entertainers and event vendors, photographers, landscapers, consultants and freelancers. Many buy because a client, venue or online marketplace asks for a certificate of insurance before a job; Thimble says it is not affiliated with those marketplaces. Crew members can be covered in a growing number of states. Larger employers, firms with significant losses, and anyone needing auto, umbrella or high property values will outgrow it.

How to buy

Online or in the Thimble app. Enter your ZIP code and activity, pick the duration and limit, and pay by card; the certificate is issued immediately. You can schedule coverage in advance, extend an active policy, and add or edit additional insureds yourself. Businesses that hire contractors can use Thimble's Certificate Manager to collect and track their subcontractors' insurance. Independent agents can sell Thimble through its broker program.

Thimble has no customer service phone number, which it says keeps prices down. Support is by live chat and an email form, Monday to Friday, 9 a.m. to 6 p.m. Eastern.

Claims

Thimble does not pay claims; the issuing carrier and its administrator do. Anyone, including an injured third party, can start a claim on Thimble's Report a Claim page with the policy number, or a policyholder can start one from the account menu. The help center lists who handles what by policy prefix:

• VFMK (Markel Insurance Company): Markel claims.
• IBL (National Specialty Insurance Company): claims submitted after June 1, 2026 go to Reserv; earlier non-cyber claims are with Sedgwick; cyber-related losses go to Tokio Marine HCC.
• EIG, WC or DWC (EMPLOYERS/Cerity workers' comp): EMPLOYERS.
• CBB, CSB or CCB (Benchmark or Spinnaker BOP): Coterie Insurance Agency.

The claims phone numbers are in the contact table below. Do not admit fault to the claimant, and keep claim documents between you, the carrier and its adjusters.

Financial strength and ratings

As an agency, Thimble has no financial strength rating; Arch's ownership does not put Arch's balance sheet behind policies issued by other insurers. The rating that applies is the issuing carrier's. Thimble describes Markel Insurance Company and National Specialty Insurance Company as rated A (Excellent) by AM Best, and Markel's profile records an AM Best A (Excellent) rating as of September 2026. For a BOP or workers' comp policy, check Benchmark, Spinnaker or EMPLOYERS on your declarations page. Thimble does not publish results, and Arch reports it inside its insurance segment. It is not ranked in J.D. Power's small commercial study.

Strengths and weaknesses

Thimble is the quickest way for a freelancer or one-person trade to get a general liability certificate for one job or one month without paying for a full year, and since 2023 it has had a large specialty insurer as its owner. It is not built for growing businesses that need advice or a full program.

• Strengths: Coverage from one hour with a $5 minimum premium; no deductible, primary and non-contributory wording, and free additional insureds; GL available in every state on Markel group paper; Certificate Manager for businesses that hire contractors.
• Weaknesses: No phone support; narrow product set with no commercial auto or umbrella; BOP and professional liability limited by state; claims handled by different administrators depending on policy prefix, which can confuse a first-time claimant.

How to contact Thimble