Thimble

First: what a certificate of insurance actually is

You don't have insurance. You have one Saturday of work. And every insurance site you open wants to sell you a year of coverage for a business that is, so far, exactly one gig long. An annual policy for one Saturday feels absurd, because for one Saturday it is.

Thimble is the company built for exactly this moment. It sells business insurance by the hour, the day, or the month, through an app or a website, and it emails you the certificate the venue is demanding right after you pay. Thimble's own COI explainer claims the whole quote-buy-certificate loop takes under a minute. That speed claim is Thimble's, not ours, though the independent reviews below mostly back up the buying experience. This article is part of our resources directory; Thimble holds the on-demand slot on our insurance shortlist with a verified 4.41 out of 5.

One thing to know up front: Thimble is not an insurance company. It's a licensed broker, and the actual policies are issued by big, boring, A-rated insurers, Markel and National Specialty. Not a scandal; that's how much of modern insurance works. But it changes who handles your claim, so it gets a whole section below.

A certificate of insurance (everyone says "COI") is a one-page document proving your business carries insurance. The standard format is called an ACORD 25, and it lists who's insured, what type of coverage (general liability, usually), the dollar limits, and the policy's start and end dates. That's it. It is not the policy itself; it's the receipt the venue keeps on file so that if your extension cord trips a guest, their lawyer calls your insurer instead of their landlord.

Venues ask for it because their own insurance and their lease usually require it. The "naming us as additional insured" part means your policy briefly extends its protection to the venue too, for claims arising out of your work there. Traditional brokers can take days to issue these; Thimble's model is the opposite: unlimited COIs at no cost, and unlimited additional insureds added instantly, per its own help pages. For someone whose entire insurance need is "make the venue's compliance person happy by Friday," that's the product.

So the direct answer to the panicked Friday question: yes, you can buy a policy today and send the certificate today. Whether you should buy it from Thimble versus an annual insurer depends on how often this gig repeats. That math comes later.

What "on-demand insurance" means

Traditional business insurance is sold in one shape: a 12-month policy, paid monthly or up front. On-demand insurance means the policy's length matches the job instead of the calendar. Thimble sells coverage in four durations:

• By the hour or day. Coverage for a single job or event, starting and ending when you tell it to. Priced per job: enter your trade, ZIP, and dates, and the price shows before you pay. Thimble publishes no hourly rate card, so ignore any article quoting one.

• By the event. Event insurance for one-off things like markets, pop-ups, parties, and shows, purchasable by the hour or for multi-day runs, with setup and breakdown time included.

• By the month. "Thimble Monthly" is subscription-shaped: ongoing coverage, cancel anytime, and a Pause feature that suspends coverage and billing for up to 30 days, once per policy. It's built for seasonal work.

• By the year, like everyone else sells.

On price, we'll cite exactly one number, because it's the only one Thimble itself publishes: policies start at $17 a month, per its general liability cost page. Everything else depends on what you do, where you do it, and the limits you pick. We're not going to invent example premiums; any number we made up would be wrong for you specifically.

The honest framing: on-demand insurance is not cheaper insurance. Per unit of time it's more expensive, because you're paying for the right to buy only the sliver you need. It wins when the sliver is genuinely all you need.

What you can actually buy through Thimble

The lineup, per thimble.com:

• General liability (GL). The one venues ask about. Covers third-party bodily injury and property damage: the tripped guest, the stained carpet. This is the default policy for almost every service business and event vendor.

• Professional liability (PL, also called E&O). Covers claims that your professional advice or work product cost a client money. Relevant for consultants, designers, and bookkeepers. A venue won't ask for this; a corporate client's contract might.

• Event insurance. GL shaped around a specific event, with the venue named as additional insured. The standard answer to a venue's COI demand for a one-off.

• Workers' compensation. Covers your employees' work injuries. Sold through Thimble in Illinois, which has a dedicated Illinois page, though not in the four states where the government is the only legal seller (Ohio, North Dakota, Washington, Wyoming). Confirm availability inside the quote flow, since it varies more than their marketing suggests.

• Also on the shelf: a business owners policy (BOP), business equipment protection, commercial property, and cyber, none of which you need for your first Saturday, so we'll leave them there.

The Illinois part, plainly: the moment you hire your first employee, even part-time, Illinois requires workers' comp coverage, per the Illinois Workers' Compensation Commission. Knowingly skipping it runs up to $500 per day in fines with a $10,000 minimum, and corporate officers can be personally liable. Sole proprietors and LLC members can generally exempt themselves. Translation for a one-person business: you're fine without workers' comp today, and the day you hire help, even a friend you pay for one weekend, you're not. That's a state law thing, not a Thimble thing, but Thimble is one of the places that will sell you the fix.

If you're still deciding what your business legally is, sole proprietorship versus LLC, that decision slightly precedes this one, because the name on your policy should match how you operate. Our LLC setup guide walks through it.

The fine print that matters: Thimble doesn't insure you

This is the section to actually read.

Thimble, legally Verifly Insurance Services, LLC, is an insurance broker, licensed in all 50 states and DC, per its own help center. It designs the product, runs the app, takes your money, and issues your documents. But the policy, the actual promise to pay, is made by an insurance carrier: Markel Insurance Company or National Specialty Insurance Company, both rated A ("Excellent") for financial strength by AM Best, per Thimble's ratings page. Since April 2023, Thimble itself has been owned by Arch Insurance, part of Arch Capital Group, a large global insurer.

In plain words: Thimble is the storefront; Markel or National Specialty holds the paper. When someone gets hurt at your event and files a claim, the money, if the claim is covered, comes from the carrier on your policy, and the claim is worked by that carrier's claims administrator, not by the app you bought from. Thimble's claims page spells it out: Markel services its own policies' claims; National Specialty's go to a designated third-party administrator.

Is that bad? Structurally, no. A huge share of small-business insurance is sold exactly this way, and A-rated carriers are the strongest thing about Thimble's offer. But it explains the single biggest pattern in Thimble's negative reviews: people love the 60-second buying experience, then hit a claim and discover the claims experience belongs to a different company with different pacing. Thimble built the buying. It outsources the claiming. Go in knowing which company you'll actually be dealing with on the worst day.

What the reviews say, and how we got our numbers

We rate every tool in our directory the same way: independent review platforms only, weighted by review count, and any source with fewer than 25 reviews gets excluded from the average, but disclosed. All figures below were verified on September 2, 2026.

Thimble's weighted average: 4.41 out of 5, across 3,670 counted reviews.

• Trustpilot: 4.2 from 2,370 reviews. The distribution is polarized in the way on-demand insurance tends to be: 82% five-star, 9% one-star. The five-stars are overwhelmingly about speed and ease of purchase; the one-stars cluster around claims handling, consistent with the broker structure described above.

• Apple App Store: 4.8 from roughly 1,300 ratings.

• BBB customer reviews: 1.0, from six reviews. Six is not a sample. It's six people, and almost nobody goes to the BBB to report a good day. Under our 25-review minimum it's excluded from the average, but we're telling you it exists, because a directory that hides its ugliest data point isn't one you should trust.

• Google Play: we couldn't verify the rating on Google's own page on our check date, so it's omitted rather than estimated.

For context, Thimble's Trustpilot score alone clears our 4.0 bar, so the rating doesn't depend on app-store generosity.

When an annual policy beats by-the-job coverage

The framework, minus invented dollar figures.

By-the-job insurance is priced like anything sold in small units: each unit carries its own overhead. One policy for one Saturday is a great deal compared to twelve months of coverage you don't need. Fifty one-day policies a year is a terrible deal compared to one annual policy. Thimble knows this, which is why Thimble Monthly exists; the company's own product ladder concedes that steady work belongs on a longer policy.

There's also a softer cost to job-by-job coverage: the certificate shows your policy dates. An ACORD 25 from a one-day policy says, right on the page, that your insurance expires Sunday. For a market organizer, fine; that's the norm. But a property manager or general contractor comparing bids can read dates, and ongoing clients often want proof of continuous coverage, not proof that you insure yourself one Saturday at a time.

Our rule of thumb:

• One-off or rare gigs (a few times a year, unpredictable): Thimble, by the job. Paying for twelve months to cover three Saturdays is the absurdity you correctly sensed in paragraph two.

• Seasonal but steady (every weekend, May through October): Thimble Monthly with the pause feature, or start comparing annual quotes. This is the crossover zone; price both.

• Steady, ongoing work (recurring clients, weekly jobs, anything you'd call "my business is running now"): an annual policy almost certainly wins on total cost, and this is where Next Insurance, the conventional-policy pick in our directory, verified at 4.3 out of 5, is the comparison to run. The two aren't rivals so much as complements: Thimble for the gig, Next for the business the gigs turn into.

The two-quote test costs you twenty minutes: quote your next job on Thimble, quote a year on an annual insurer, divide the annual price by the number of jobs you honestly expect. The arithmetic will make the decision for you, and it'll be your arithmetic, not a marketing page's.

The honest downsides

Per-job pricing punishes steady work. Covered above, but it's the big one. Thimble is a brilliant tool for the first gig and a quietly expensive habit by the twentieth. Recheck the math every few months; the business you have in October isn't the one you insured in March.

The claims experience isn't Thimble's, and the reviews show it. The 9% one-star band on Trustpilot is heavy with claims complaints, which is exactly what the broker structure predicts: a slick front end selling policies whose hardest moments are administered by third parties. "Covered" gets decided by an adjuster at the carrier's administrator, on their timeline.

Speed is also a trap. A policy bought at 7:58am for a 9am gig is a policy you didn't read, and short-term policies carry exclusions like any other insurance. The 60-second flow is real; spend ten extra minutes anyway.

Workers' comp availability is squishier than the marketing. Illinois is offered, the four monopolistic states aren't, and Thimble's own site has hedged with availability waitlists. If workers' comp is the thing you need, confirm it's quotable before you build your plan around it.

A note from Lobi Space management

Insurance shopping goes better when it starts away from the quote forms. Sit down and write out every single process your business needs in order to succeed: the gigs, the gear, the phone, the books, the paperwork. Insurance covers some of those lines and not others, and the list is what shows you which. Not every business is designed to be the same, so be careful about buying whatever a friend from the market bought. People in our community trade recommendations constantly, and jumping in on a neighbor's referral is how a lot of wrong-sized policies get sold. Their Saturday is not your Saturday. Know what your business needs before you pay for anything, on demand or otherwise.

Where your COI meets the rest of your setup

One practical detail first-timers miss: your policy and certificate carry your business address, and COIs travel. The venue files yours, organizers forward them. If your business address is your apartment, your apartment is now in the files of every venue you've worked. A real business address, the thing a virtual office provides, keeps your home out of that stack, along with your LLC filing, website footer, and Google Business Profile.

The sequence: entity first (sole prop or LLC), then address, then a policy in the business's real name at its real address, so the certificate you send Friday matches the contract you signed Tuesday. Mismatched names are the kind of thing a venue's compliance person kicks back, and now Friday is a problem again.

The short version

If a venue is demanding a COI by Friday and this gig is a one-off: Thimble is the right tool, the certificate is real (ACORD 25, A-rated carriers), it arrives in about a minute, and adding the venue as additional insured is free and instant. If the gigs are becoming a business: keep Thimble for the odd jobs, but run annual quotes. Next Insurance is our directory's pick for that shape, because per-job pricing quietly loses to annual pricing as work steadies. Know that Thimble is the storefront and Markel or National Specialty is the insurer; that's who your claim lives with. And check the rest of our resources before you buy anything else this week.

How this article was made, in one sentence: our team did the research and the checking, AI helped us organize what needed to be covered, and every opinion and piece of advice in it is ours.

Blunt questions, straight answers

Can I buy insurance the morning of the job? Yes, that's the product. Thimble's whole pitch is quote-to-certificate in under a minute, and policies can start the same day. One caution: coverage starts at the policy's effective time, not retroactively. Buy before you load in, not after the ladder falls.

Is by-the-hour insurance real coverage or a gimmick? Real. The certificate is a standard ACORD 25, the same document an annual insurer issues, and the policies are underwritten by Markel or National Specialty, both rated A by AM Best. The gimmick test isn't the duration. It's whether a real carrier stands behind the paper, and here one does.

Who actually pays if someone gets hurt at my event? Not Thimble. Thimble is the broker; the carrier named on your policy, Markel or National Specialty, pays covered claims, and the claim is processed by that carrier's claims administrator. This is the single most useful thing to understand before buying: the app experience ends where the claim begins.

The venue wants to be an "additional insured." Is that extra? No. Thimble adds unlimited additional insureds at no charge, instantly, before or after purchase; that's on their own help pages. It just means your policy also protects the venue for claims arising from your work there. Venues ask for it routinely; it's not a red flag or a shakedown.

What address goes on my COI? My apartment? Whatever address your business uses, which is exactly why it shouldn't be your apartment. COIs get filed, forwarded, and shared. A virtual office address keeps your home out of that paper trail and matches your LLC filing and contracts, the consistency a venue's compliance check actually looks for.

Do I need an LLC before I can buy business insurance? No. Sole proprietors buy insurance under their own name every day, and for a first gig that's fine. But the named insured on the policy should match how you operate: if you form an LLC, the LLC should be the named insured on future policies, or you've insured a person while the venue contracted a company. Entity first, then policy.

Why is Thimble's BBB rating 1.0 when you rate it 4.41? Because six angry people are not a dataset. Our methodology excludes any source under 25 reviews, and Thimble's BBB page has exactly six, versus 2,370 on Trustpilot and about 1,300 on the App Store. We disclose the 1.0 anyway because hiding it would be worse. If the BBB count ever grows large and stays that low, our rating changes.

One last thing

From the Lobi Space team, before you go buy a policy. On-demand coverage, annual coverage, apps, brokers: all useful tools. But a tool without a road map, a goal, and a plan behind it is just shooting in the dark, or chasing a dream. Plan the business first. Then insure the plan.

Why it made our list

• You can buy coverage for a single Saturday event and have the certificate of insurance in hand before the venue asks twice.
• General liability, professional liability and event coverage by the hour, day or month fits gig work and side businesses that an annual policy overshoots.
• It is a broker, not the carrier — established insurers like Markel hold the actual paper, which is worth understanding before you buy.