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Last updated: July 2026. Disclosure: our content isn’t financial or insurance advice – do your own due diligence before buying a policy. Some links below are affiliate links; if you get a quote through them we may earn a commission at no extra cost to you. This doesn’t affect our assessment.
Most business insurance is sold in one shape: a 12-month policy you pay for whether or not you actually work every month of the year. Thimble built its whole business on breaking that mold. It lets a freelancer, contractor, or small team buy coverage by the hour, the day, the month, or the year – entirely online, in about a minute – and generate proof of insurance on the spot. For anyone whose work comes in bursts rather than a steady year-round stream, that flexibility is the entire appeal.
Founded in 2016 (originally as Verifly) and rebranded to Thimble in 2019, the New York–based company was acquired by Arch Insurance in 2023, giving a nimble insurtech the backing of a major global carrier. This review covers what Thimble offers, what it costs, how customers rate it, and exactly who it suits – and who should look elsewhere.
Get covered in about 60 seconds
Thimble lets you quote, buy, and download proof of insurance online – by the job, the month, or the year. Pay only for the coverage you actually use, and pull an unlimited number of certificates of insurance for free. See your own price before you commit.
Get a Free Thimble Quote →Quick company snapshot
| Company | Thimble (Verifly Insurance Services, LLC) |
|---|---|
| Founded | 2016 as Verifly; rebranded Thimble in 2019 |
| Headquarters | New York, NY |
| Ownership | Arch Insurance (Arch Capital Group) – acquired 2023 |
| Underwritten by | Markel Insurance Co. & National Specialty Insurance Co. – AM Best A (Excellent) |
| Coverage types | General liability, professional liability (E&O), BOP, business equipment, workers’ comp, event, cyber, drone |
| Business types served | 300+ |
| Policies issued | 170,000+ (since 2018) |
| Starting price | From about $5/hour or ~$17/month (general liability) |
| Availability | All 50 U.S. states (some lines vary by state) |
| Trustpilot | ~4.2 / 5 (2,200+ reviews) |
| App ratings | 4.8 / 5 (Apple App Store & Google Play) |
| Website | www.thimble.com |
Thimble at a glance
The pitch is speed and flexibility. Instead of a broker call and multi-day underwriting, Thimble quotes, binds, and issues a policy in a single sitting – often in under a minute. A wedding photographer can switch on a policy for one event weekend; a handyman can carry monthly general liability only through the busy season; a brand-new consultant can add professional liability the day a contract requires it. Because everything is self-serve, you’re rarely waiting on anyone.
Just as important is who stands behind the promise. Thimble is a managing general agent, not the risk-bearing insurer – its policies are underwritten by Markel and National Specialty, both rated A (Excellent) by AM Best, and the whole operation now sits under Arch Capital. That answers the old worry about insurtech startups: the paper behind your policy is financially strong. For the full field of options, see our guide to the top business insurance companies in America.
Pros & cons
| ✅ What works in Thimble’s favor | ❌ Where Thimble falls short |
|---|---|
| Truly on-demand – buy by the hour, day, month, or year | No phone support; help is email/chat only |
| Quote-to-coverage in about 60 seconds, all online or in the app | Claims run through third-party administrators; some slow-processing complaints |
| Instant, unlimited certificates of insurance – add additional insureds free | Annual cancellations use short-rate math, so refunds are small |
| Low entry cost; you pay only for coverage you actually use | Professional liability is often bundled, raising the headline price |
| A-rated paper (Markel), now backed by Arch Capital | Limited customization – not built for complex or large operations |
| Highly rated app (4.8) and 300+ business types, plus niche lines like events and drones | Small-sample BBB customer reviews skew low despite the A+ grade |
Coverage and products
Thimble covers the core lines most small businesses need and several that on-demand workers specifically want. General liability handles third-party injury and property damage; professional liability (E&O) protects against claims of professional mistakes; a Business Owner’s Policy bundles liability with property. On top of those sit business equipment and tools coverage, workers’ compensation, event/special-event liability, cyber, and even drone insurance – a lineup clearly built for freelancers, tradespeople, and gig workers rather than large corporations.
The standout feature is the certificate of insurance experience: they’re instant, unlimited, and free, and you can add an additional insured yourself in seconds – exactly what a contractor needs before a client will let them on site. If you run a one-person operation, our guide to the best sole proprietor insurance policies is a useful companion read.
How much does Thimble cost?
Thimble markets short-term general liability from about $5 an hour and monthly coverage from roughly $17 a month, but those are entry points for the lowest-risk profiles. Independent reviews put the blended real-world average closer to ~$94 a month, with the exact figure driven by your trade, revenue, location, claims history, and coverage limits. There are no upfront deposits, and you pay as you go rather than in one annual lump sum.
A couple of trade-offs are worth knowing before you buy: professional liability is frequently bundled in, which roughly doubles that starter price, and annual policies cancelled early are refunded on a short-rate basis, so you won’t get a clean pro-rated refund. Because pricing is so profile-dependent, a live quote is the only number that really means anything. For property-heavy operations, it’s also worth cross-shopping specialists – see our list of hazard insurance companies for small business.
See your exact price in about a minute
Because rates depend so heavily on your trade and how often you work, the only number that matters is your own. Thimble’s quote tool is free, takes about a minute, and never requires a phone call.
Check Thimble’s Prices →Customer experience and ratings
Thimble’s reputation is genuinely strong for an insurer. It holds around 4.2 out of 5 on Trustpilot across 2,200-plus reviews, and its mobile apps score an excellent 4.8 on both the Apple App Store and Google Play – a sign that the self-serve experience, which is the whole product, actually works. Its BBB profile carries an A+ rating.
The praise is consistent: buyers love how fast they get covered and how easily they can pull a certificate of insurance on demand. The criticism clusters around a few themes – there’s no phone line if you have a nuanced question, claims are handled by third-party administrators and can feel slow, and a minority of buyers are caught out by exclusions or short-rate cancellation refunds they didn’t read closely. (Note that BBB’s customer-review star average sits low, but on a very small sample.) The practical takeaway: because no agent walks you through the fine print, read your exclusions and cancellation terms before you buy. To see how self-serve carriers compare more broadly, our NEXT Insurance review covers a close competitor.
How Thimble compares
| Factor | Thimble | Traditional carrier / broker |
|---|---|---|
| Speed to bind | ~60 seconds, online | Hours to days |
| Term flexibility | Hour, day, month, or year | Usually 12-month only |
| Human guidance | Limited, self-serve | Dedicated agent |
| Entry price | Low; pay-as-you-use | Often higher, annual |
| Complex / high-value risk | Weaker fit | Stronger fit |
| Certificates of insurance | Instant, unlimited, free | Varies |
Thimble sits firmly in the digital-first camp, competing with the likes of NEXT Insurance and marketplaces such as Tivly rather than agency-based carriers. Its edge is unmatched term flexibility for short and seasonal work; its weakness is hands-on service for complex risks.
Who Thimble is best suited for
Worth a closer look if you are:
- A freelancer, independent contractor, or handyman who wants affordable coverage fast
- An event, seasonal, or gig worker who only needs coverage some of the time
- Someone who needs certificates of insurance on demand to satisfy clients or venues
- Comfortable managing a policy from an app rather than over the phone
- Reassured by A-rated (Markel) paper now backed by Arch Capital
Consider alternatives if you are:
- Running a larger or growing business that needs complex, long-term, customizable coverage
- Looking for a dedicated agent to advise you and advocate at claim time
- In need of employee benefits or robust in-house claims handling
- The type who wants every exclusion walked through before committing
Ready to check your rate?
Thimble is one of the most flexible digital options on the market for freelancers and project-based businesses – fast, affordable, and backed by A-rated paper. A quote is free and takes about a minute.
Get Your Free Thimble Quote →Final verdict
Thimble does exactly what it set out to do: make small-business coverage fast, flexible, and manageable from your phone. With Markel’s A-rated paper and Arch Capital now behind it, the old knock on insurtech startups – will they be around to pay claims? – no longer applies. The honest caveats are about service, not solvency: light human support and pay-as-you-go fine print mean the responsibility to understand your coverage sits with you.
For freelancers, contractors, and event or seasonal businesses that value speed and “pay only for what you use,” Thimble is a genuinely strong choice – and our pick for the best on-demand coverage in our business insurance companies guide. Businesses with complex or high-value exposure should weigh it against agent-led carriers first. If it sounds like a fit, the fastest way to know is to run a free quote – check your specific limits and exclusions, and you’ll know within minutes whether the terms work for you.
Affiliate disclosure: some links on this page, including the “Get a Free Thimble Quote” buttons, are affiliate links marked nofollow. If you get a quote or buy a policy through them, Sophisticated Investor may earn a commission at no additional cost to you. This does not influence our editorial assessment. Figures and ratings (including AM Best ratings and pricing) are accurate to the best of our knowledge as of July 2026 and may change. This article is for informational purposes only and is not insurance or financial advice.
