Thimble Insurance Review

If you’re searching for an insurance company that caters to small businesses, you might want to look at Thimble Insurance. After reading about it in Money magazine, I’d recently heard of it and recommended that a friend of mine check it out for their own business. He currently runs a landscaping company and was having trouble finding a traditional insurance company that didn’t require him to pay high premiums all year long, even during the months when he wasn’t working.  

Thimble understands these challenges and works to find solutions to meet the unique needs of all types of businesses. Here’s an overview of Thimble Insurance and several things you’ll want to consider when determining if it’s the right Company to provide coverage for you. 

History of the Company

Thimble hasn’t been around very long, but it’s already gained a strong following in the several years it’s been available. Founded the Company in 2016 by Jay Bregman and Eugene Hertz, the Company’s initial goal was to sell “daily insurance” options to drone operators instead of requiring them to purchase unnecessary policies they didn’t need.

Since this initial offering, the Company has grown significantly and now offers coverage to over 300 types of small businesses. They also pride themselves on making the insurance buying process less complicated for business owners and seek to make it simple, scalable, and flexible.   

In fact, the Company makes an excellent choice for contractors and gig workers, as it offers options for monthly, daily, and even hourly coverage. 

Size and Reputation 

The Company is popular with business owners looking to purchase policies for the first time or who are just starting with their business and want to ensure that they are adequately covered. Notably, 75% of Thimble’s customers are first-time business insurance buyers. This fact shows that the Company is becoming a trusted name for those not well-versed in the complicated process of buying insurance policies. 

Since it started in 2016, the business has sold over 200,000 policies for over 60,000 businesses and continues to grow. They receive strong marks in customer reviews on sites such as Trustpilot, Delighted, and the App Store & Google Play. 

Most of their policies are underwritten and backed by Markel Insurance Company and National Specialty Insurance Company. Markel Insurance is a Fortune 500 company, and National Speciality Insurance is a State National Insurance Company subsidiary. Both companies have an “A” rating for financial strength through A.M. Best. Global Aerospace and several other companies underwrite Thimble’s drone policies. 

Overview of Types of Thimble Insurance Offers

A quick glance at the Thimble website shows that they offer a good selection of the most-needed business insurance products and even some more unique and specialized options. These options meet the needs of over 120 different types of businesses and are available to purchase for customers in all 50 United States.  

The “What We Cover” section lists the following available products: 

  • Small Business Insurance 
  • General Liability Insurance 
  • Professional Liability Insurance 
  • Errors & Omissions Insurance 
  • Business Equipment Insurance 
  • Business Owners Policy (BOP) 
  • Commercial Property Insurance 
  • Workers’ Compensation Insurance 
  • Event Insurance 
  • Drone Insurance 

All policies purchased instantly include a Certificate of Insurance (COI) that provides customers with proof of an active, valid insurance policy that they can share with their clients to provide peace of mind. Sometimes you will also hear this document referred to as an ACORD 25 form. Thimble notes that it’s easy for their customers to share this vital document using the Thimble app to email or text it directly to the client. 

Thimble Insurance Cost 

Many customers find that the cost of a policy through Thimble Insurance works well for their unique business needs. Small businesses often need to be budget-conscious, and Thimble’s General Liability Insurance starts at $17 a month, with the average business owner paying about $42 a month of coverage. They even offer short-term policies that start at $5 for up to $1,000.000 of coverage. You must complete an online quote to obtain their pricing options.  

My landscaper friend’s policy fell into this budget, and he agreed that the cost was very competitive compared to some of the other local quotes he’d received, even from more prominent and established companies. 

A few customers have questioned whether the quick process for quoting and purchasing insurance gave them the best price they could have obtained or if they may have purchased options they didn’t need. Still, overall most people agreed that the costs were suitable for the convenience and ease of getting a policy. 

Claims Processing and Customer Service

One thing that is most important to remember for customers who purchase their insurance through Thimble is that the Company does not actually underwrite the policies. They act as the middleman between the Company that writes the policy and the customer. 

You can submit your claim through Thimble, and they send it to the proper underwriting company on your behalf. Some customers may find having this type of “middleman” burdensome and would rather deal directly with the Company that writes their policy. 

Regarding customer service, Thimble does not offer options for customers to contact them by phone and doesn’t have in-person agents you can meet with to ask questions or discuss policies. All customer support is online and mostly done through emails and typically only during business hours of 9:00 AM to 6:00 PM EST. They do also offer a FAQ section, where customers can find answers to common questions without having to contact support. However, it can be frustrating for customers not to have someone instantly available to speak to when they need assistance. 

In fact, customer service is the one area where Thimble consistently receives the most negative reviews. Many customers would have appreciated a phone or live chat option to quickly and efficiently contact someone from the Company. 

Website And Mobile App

The Thimble website is straightforward to navigate. Existing customers can easily log in to their accounts directly through there, and potential customers can efficiently complete the process to get a quote and purchase insurance. You can also quickly learn about the available insurance offerings and check your insurance requirements by state.   

Existing customers can do most of their business with Thimble through the Mobile App (available for both Apple and Andriod). Customers find that the app is easy to navigate and also easy to add insurance, submit claims, and obtain/share a Certificate of Insurance. 

The app has a high rating in both the Apple Store and Google Play Store, with customers stressing that it is easy to use and provides them with all the tools they need to obtain insurance for their business quickly.  

How to Get a Quote With Thimble Insurance

As mentioned, getting a quote with Thimble is a very easy process. My landscaper friend was satisfied with the overall process and commented on how quick it was to go through it, obtain a valid quote, and purchase the needed coverage.  

You can obtain a detailed quote directly through the website or by downloading the mobile app. Click the “Get a quote” button, and the system will navigate you through a series of simple questions to provide you with a customized quote for the coverage you need.  

During the quote process, you choose your type of work and the activities you will perform, choose the limit for the policy you wish to have, and identify the size of your crew (if applicable). You’ll instantly see prices for your selected options based on the hour, day, and month. Decide which kind of options works best for your current needs and determine when to start and stop the policy (down to the hour). 

If you need any other options, you can add them during the “Add-Ons” section, and you also have the choice to add “Additional Insureds instantly.” 

Thimble Insurance Pros and Cons 

Many customers are quite happy with their policies purchased through Thimble. However, there are several areas where the Company could use some overall improvement. Here’s a quick list of some pros and cons of purchasing business insurance through Thimble. 


  • Easy to get a quote and purchase a policy in minutes through the website or the app. 
  • Instant COI is available to share with clients after purchasing a policy. 
  • Customizable coverage allows users to purchase monthly, daily, and even hourly coverage. 
  • Coverage is available in all 50 United States. 
  • Policies are underwritten and backed by companies with strong financial strength ratings. 
  • Coverage can start as little as $5.00. 
  • Thimble covers over 120 different types of small businesses and their unique needs. 
  • Apple and Andriod App is easy-to-use and provides customers with everything they need for managing their policy, including extending, canceling, or modifying coverage. 


  • Customer service is only online through email, and customers cannot speak directly to a representative by phone or live chat. 
  • Some customers say they ended up purchasing policies they didn’t need and, therefore, overpaid for their coverage. 
  • Some types of businesses still cannot find coverage to meet their needs through Thimble. 
  • Before making a purchase, there is no way to discuss policies and their features with a live person. 

What Types of Customers Should Consider Thimble?

Thimble makes an excellent option for small businesses who need insurance at the last minute, periodically, or who have unique types of businesses that other companies can’t service. 

Larger companies will likely not find that Thimble is a good fit for their business insurance needs, especially those with more than 50 employees or who earn more than $10 million in revenue. These companies will also likely need more customized support and dedicated agents for claims processing, which Thimble cannot provide.   

It’s an excellent option for service providers that work events like D.J.s, personal chefs, magicians, food/catering, etc. If you’re a general construction contractor, you’ll also find that their services work well for this type of business. The same applies if you’re a landscaper, like my friend who tried out the Company. 

Other small businesses like crafters, personal trainers, pet walkers, photographers, and hair stylists will also find policies that work with Thimble. The Company covers many different types of people and business owners, so it’s unlikely for small business owners not to find something to meet their needs. Of course, they also continue to offer their original drone operator’s policies, which is hard to find with many other insurance companies. 

Other Similar Companies 

Several other companies offer similar options to Thimble and a similar pricing structure. The closest overall competitor is Next Insurance which provides similar insurance offerings for small businesses and has policies underwritten by Munich R.E. However. Next is not as flexible as Thimble. It only offers policies by the month, with no options for daily or hourly policies.

Other names to check out for this type of small business insurance include Embroker, biBerk, and Hiscox. Availability for many of these offerings depends on the state in which you reside, and quotes vary depending on the insurance type and amount of coverage needed. 

Final Thoughts on Thimble

If you’re a gig worker or a small business owner needing flexible and on-demand insurance, it is worth looking at Thimble Insurance and its offerings. Its affordable coverage allows businesses, contractors, and gig workers to provide their clients with peace of mind knowing they have coverage in the event of unforeseen circumstances.   

In addition, the Company has many highly-satisfied customers and a good rating for their mobile app. It makes it very quick to obtain the needed coverage without going through hoops or lengthy quoting processes. It’s a good option for those who know the coverage they need and want to get it quickly. 

In addition, the Company has many highly-satisfied customers and a good rating for their mobile app. It makes it very quick to obtain the required coverage without going through hoops or lengthy quoting processes. It’s a good option for folk who know the coverage they need and want to get it quickly. 

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