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Alex Goldberg

In this Article

In this Article

About the Author

Alex Goldberg

Alex is a growth marketer, behavioral economics buff, and lover of all things Direct-to-Consumer. He enjoys scaling early-stage companies and working to bring transparency to opaque industries. He is a UC Berkeley grad, an aspiring retired golfer, and an avid soccer fan.

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Next Insurance vs Thimble vs Huckleberry: What’s Best for SMBs?

In this Article

Alex Goldberg

Workplace accidents can happen at any time. According to the U.S. Bureau of Labor Statistics, 4,764 fatal work injuries were reported in 2020. For this reason, business owners must take proactive safety measures to avoid all sorts of accidents in the business environment.


It is also crucial for business owners to get their business insured to avoid potential risks, but how can they tell which insurance company is the best for their company and employees while minimizing cost and maximizing coverage?


75% of U.S. businesses are underinsured, while 40% of small business owners don’t have any type of insurance at all. This leaves us wondering: What is the best online small business insurance company in 2022?


In this post, we will review the top three online small business insurance companies: Next Insurance vs Thimble vs Huckleberry. We’ll compare their coverage types, policies, quotes, customer service and financial strengths, and even gather real customer reviews to help you find the best insurance provider for your small business.


TLDR: which SMB insurance do we recommend?


Short on time? Here are our top recommendations:


Choose Next Insurance if you want an online insurance company that handles its own claims and values customer support.  Choose Thimble if your priority is last-minute bookings and you want a variety of coverage plans (ex: by job, month or year).  Choose Huckleberry if you want to compare coverage packages from different insurance companies in one platform, and don’t mind online support only. 

But don’t just take our word for it! Read on to learn how Huckleberry, Next, and Thimble stack up on a granular level, to determine if your business is a good fit.



But first, does your small business really NEED insurance? 

Every business, small and large, needs efficient insurance coverage. It helps business owners cover the costs linked with property damage, liability claims or workers’ compensation – you never know what could happen, and preparation is key.


In short, the right type of business insurance can help you avoid out-of-pocket payments for costly damages and legal claims against your company. 


Source: Thimble


The Insurance Information Institute suggests small businesses purchase the following four basic types of insurance:


General liability insurance


Unfortunately, any person associated with your business can sue you. For instance, customers could claim that your company has caused them monetary loss with a defective product. Similarly, couriers could allege that your business environment is hazardous. 


The general liability insurance covers any lawyer’s fees and any costs incurred in courts, settlements and judgments.


Property insurance


If any property (building, inventory, machinery, electronic devices, raw materials, etc.) in your business is damaged due to fire or theft, property insurance can help you cover it. This includes any costs incurred in the equipment breakdown, removal of debris, water damage or other losses.


Workers’ compensation insurance


The need for workers’ compensation insurance depends on the structure of your company. Three or more employees – for example – require it more than a 2-person business working from home. This compensates employees for medical care by replacing a part of lost wages in the case of an injury during their course of employment, regardless of the cause of injury. If the worst were to occur in the workplace, the insurance company would compensate the employee’s family. 


An equally essential factor to consider for your employees is their retirement plan. Check out our review of Vestwell, a popular SMB 401(k) provider to learn more about this coverage.


Business auto insurance


Another insurance that depends on your company structure is business auto insurance. This covers any costs incurred in the injury or property damage to third parties caused by your business’ vehicle.


Some other kinds of business insurances to consider:


  • Professional liability insurance: Compensates customers or clients for a workplace injury or financial loss and covers any legal fees.
  • Cyber liability insurance: Compensates customers and clients should their personal information be exposed in a data breach and covers legal expenses, credit monitoring and cyber extortion.
  • Employment practices liability insurance (EPLI): Compensates current, past and future employees should they experience workplace harassment or other violations, and covers any legal costs.
  • Directors and officers insurance (D&O): Compensates employees and third parties for any failure to meet regulations, fulfill duties, or for misuse of funds, and covers any legal costs incurred.


Comparing online small business insurance: Next Insurance vs Thimble vs Huckleberry 


Next Insurance vs Thimble vs Huckleberry: What’s the Best Small Business Insurance?

Quotation time Minutes Minutes Minutes
One place user-interface Website and mobile app Website and mobile app Website
Industrial standard coverage Tools and equipment insurance Drone liability

Business equipment protection
Hired and non-owned auto insurance

Employment practices liability insurance

Spoilage coverage insurance

Employee dishonesty insurance
Process of application and filing Easy Easy Easy
Types of insurance offered General Liability Insurance

Commercial Property Insurance

Workers’ Compensation Insurance

Commercial Auto

Tools & Equipment

Business Owner’s Policy

Professional Liability/E&O
General Liability Insurance

Commercial Property Insurance

Workers’ Compensation Insurance

Professional Liability/E&O

Business Equipment Protection

Event Insurance

Business Owner’s Policy

Drone Insurance
General Liability Insurance

Workers’ Compensation Insurance

Commercial Auto

Business Owner’s Policy
Add-ons coverage options Hired & Non-Owned Auto Insurance

Liquor Liability insurance
Hired & Non-Owned Auto Insurance

Business Interruption Insurance

Equipment Breakdown

Product Liability

Cyber Insurance
Business Interruption

Business Property

Professional Liability

Liquor Liability

Restaurant Endorsement

Employment Practices & Dishonesty 

Spoilage Coverage

Equipment Breakdown 
Underwriters (risk managers of the organization) Munich Re

NEXT Insurance US company 

State National Insurance Company, Inc.
Markel Insurance Company

Global Aerospace
AmTrust Financial

Berkshire Hathaway GUARD Insurance Companies



The Hartford

Markel Insurance Company

Availability of customer support Call, email, and app. Email-only May take 2 days to reply to customer queries.
Discounts? ✅ 10% discount on bundled policies
Availability 49 U.S. states (excluding New York) 50 U.S. states 48 U.S. states (excluding Wyoming and South Dakota)



Next Insurance vs Hiscox

The main difference between Next Insurance and Hiscox is the online user experience that Next offers, creating easier and more constant ways to communicate with agents and brokers. Hiscox is popular among small businesses, with very legitimate underwriting and policy options, but their technology isn’t’ as intuitive nor modern as Next’s. 


Next Insurance, Thimble and Huckleberry differ from Hiscox in their emphasis on technology, offering ease of use as a business owner. Switching to Next Insurance might be worthwhile if you’re looking for the most affordable policies as well, as Hiscox has to support the overhead of brick and mortar locations, brokers, and other legacy infrastructure. Moodern, digital-first business insurance providers  like Next, Thimble and Huckleberry make it super easy to do everything online, from policy selection to paying premiums to making adjustments to your coverage.



Review of Next Insurance


Source: Next Insurance 


Next Insurance is a newcomer to the online business insurance market. The company, founded in 2016, provides services similar to other insurance companies, such as speedy approval, price quotation, and essential products.


Next Insurance is a Better Business Bureau (BBB) accredited company with an A- rating, and its highly customizable offerings provide a distinct advantage over its competitors. This enables it to meet the demands of organizations ranging from construction to child care to fitness and beyond.


The company provides transparent rates with no hidden charges or deductibles. Next Insurance also offers a fast quotation within 5 minutes, a live certificate for instant proof of insurance and monthly payments at no extra cost. There will be no more back-and-forth or phone tag – just quick and simple COIs for busy people like you and your clients.


As of yet, the company claims to provide insurance coverage to more than 300,000 small businesses.


What kind of insurance does Next offer? 


Source: Next Insurance 


Next Insurance provides a variety of plans that may be purchased individually or in bundles for up to a 10% discount. In general, low-risk businesses, such as web publishers, may pay less for insurance than high-risk businesses like construction.


Next Insurance offers the following  insurance types for small businesses:


What kind of business insurance does Next offer? Next’s coverage Price
Business Owner’s Policy  Combines General Liability Insurance and Commercial Property Coverage  Depends on individual business 
General Liability Insurance  Bodily injury, property damage, advertising harm, court and legal fees, medical payments, libel, slander & defamation As low as $25/month
Worker’s Compensation Insurance  Medical expenses, lost wages, survivor benefits, retraining, permanent injury, employer’s liability As low as $14/month 
Commercial Property Business goods and gears, inventory, buildings, equipment breakdowns, business income interruptions As low as $17/month
Business Personal Property Insurance  Equipment and supplies damage, inventory damage, furniture and upgrades damage As low as $18/month
Commercial Auto  Underinsured motorists, rental reimbursement, towing & labor, collisions & comprehensive coverage, injuries, property damage As low as $25/month
Professional Liability Business errors, missed deadlines, accusations of negligence  As low as $18/month

In addition to these, Next Insurance also provides Tool & Equipment Insurance, Errors & Omissions, Liquor Liability, etc. They have insurance policies for various specific professions including contractors, consulting, construction, cleaning, entertainment, education, beauty, fitness and therapy. That’s pretty awesome if your business sits within one of these industries!


Next Insurance understands how difficult it can be to choose the necessary coverages, which is why they’ve created an easy, fast online instant quote process. In less than 10 minutes, you can review their personalized recommendations and modify them to match your business needs. Contrast that with a traditional back and forth with a broker, and it’s no wonder Next has been growing so fast.



How to apply for Next Insurance


Next’s application process is super easy and simple. You can apply through their newly-launched app or visit Next Insurance’s official website. In addition, the instant quote feature makes everything easy – from buying a policy, filing a claim and getting an insurance certificate online. 


It also lists everything your insurance does not cover before providing you with a quote. Next Insurance takes pride in its transparency, as there are few things more unpleasant than filing a claim with your insurance carrier just to find out something isn’t covered.


Because Next Insurance may want digital copies of your business documents, it’s a smart idea to acquire the following information before beginning your online application:


  • Your annual sales numbers, as well as basic company information
  • Details on the construction of any structures you own, including age, material and square footage, if applicable.
  • The number of employees on your team, as well as their job titles (in some states, contractors may be required to have workers’ compensation insurance).
  • For corporate car or fleet insurance, you’ll need to describe your vehicle types, VIN numbers, and any drivers.
  • Any previous insurance claims submitted by your company.



How much does Next Insurance cost?

Next Insurance offers monthly policies starting at just $11 for some professionals, and less than $3 daily for others.. Once you fill out the application and request a quote, the company will provide you with the prices – you’ll receive three quotes and three levels of coverage to select from in minutes, which is unrivaled in terms of speed and efficiency.



How to file a claim with Next Insurance

You can file a claim online or call the contact number mentioned on Next Insurance’s website. The representative will ask you the reason for your claim and request any related photos and documentation. They’ll then review your claim and get back to you as soon as possible.



Next Insurance reviews: What customers are saying? 

Next’s customers consistently reaffirm the company’s claims: convenient, affordable, quick and easy solution, compared to traditional insurance companies. Most people don’t like dealing with insurance, so it’s refreshing to see so much positivity.



Source: Facebook



Review of Thimble small business insurance


Source: Thimble


Headquartered in New York City, Thimble, previously known as Verifly, originally offered liability insurance to drone operators. It now provides essential insurance to over 300 small business professionals, such as handymen, pet sitters, D.J.s, beauticians and more with an A+ rating from the BBB.


The credits for Thimble’s general liability policies go to Markel Insurance Company, a Fortune 500 company, and the company’s drone policies are backed by several insurance companies, underwritten by Global Aerospace.



What kind of business insurance does Thimble offer?


Thimble offers the following insurance types for small businesses:


Thimble’s SMB Insurance type What it covers
Business Owner’s Policy Combines General Liability Insurance and Commercial Property Insurance 
General Liability Insurance  Bodily injury, property damage, personal & advertising injury
Worker’s Compensation Insurance  Employee accident or injury, employee illness, employee disability, repetitive stress injury
Commercial Property Buildings, business contents, building exterior, indoor & outdoor property, equipment, business interruption 
Professional Liability Actual or alleged insurance, defense of claims, false or frivolous claims for damages
Event Insurance (for events lasting up to 2 weeks) Event liability, liquor liability

Thimble also offers Errors + Omissions Insurance, Business Equipment Insurance, Cyber Insurance, Product Liability Insurance, Auto Liability Insurance, Business Interruption Insurance, Equipment Breakdown Coverage and Hired & non-owned auto coverage. 


Staying true to its’ roots, Thimble also provides an on-demand liability insurance service for drone operators via the Verifly IOS and Android app. For drones, it delivers one, four and eight-hour policies, along with up to $10 million in liability coverage. 


How to apply for Thimble insurance


Source: Thimble


To get a quote from Thimble, start by entering your business details accurately and you’ll receive a quote within minutes. Thimble will then recommend different types of coverage based on your details provided and you’ll determine the policy parameters you want. 


Some coverage options include choosing to pay premiums annually rather than monthly (which can save you some money) or adding additional insureds to your coverage. As soon as the first payment is made, the company instantly issues the certificate of insurance, and coverage starts the same day. 


How much does Thimble cost?

Thimble is less expensive than many small company insurance carriers because of its emphasis on flexible policy terms. The quote tool is the only way to determine your price range but is an easy way to get an estimate, which start at $5.00.


How to file a claim with Thimble

Claims are filed with one of Thimble’s underwriters – Markel Insurance Company or National Specialty Insurance Company. Additionally, Thimble’s customer service is solely available online, which may be a consideration if you prefer to speak over the phone with a representative. You can generally access a rep 24/7, but only via instant messenger or email.



Thimble reviews: What customers are saying?

Thimble clients appreciate the variety and flexibility of insurance packages, which avoids committing to anything they don’t want.



Source: Trustpilot



Review of Huckleberry small business insurance


Source: Huckleberry


Huckleberry is not an insurance provider like Next or Thimble, but instead acts as a broker that serves as a bridge between business owners and insurance carriers with coverage package options. With this model, they offer simple, easy and quick insurance services to small business owners.


Today, Huckleberry partners with many respected business insurance prorviders including AmTrust Financial, Berkshire Hathaway GUARD Insurance Companies, Chubb, EMPLOYERS, The Hartford, Markel Insurance Company, and….you guessed it: Hiscox.



What kind of business insurance does Huckleberry offer?


Huckleberry offers the following insurances for small and medium sized businesses:


Huckleberry Business Insurance What it covers
Business Owner’s Policy  Combines General Liability Policy, Business Interruption Insurance, and Business Property Insurance 
General Liability Insurance  Bodily injury, property damage, reputation harm, advertising injury 
Worker’s Compensation Insurance  Medical expenses & lost wages
Commercial Auto  Scheduled vehicles, owned vehicles, hired & non-owned vehicles, equipment coverage

Huckleberry offers additional services including hired and non-owned auto insurance, employment practices liability insurance, spoilage coverage insurance, employee dishonesty insurance, interruption insurance, professional liability insurance, liquor liability insurance and restaurant endorsement insurance.



How much does Huckleberry insurance cost?

Because Huckleberry does not directly provide insurance, premiums will differ depending on your coverage requirements and the provider you are matched with, which does not include broker fees.


What is Huckleberry’s application process like?

I think we’re seeing a trend: submitting an online application to receive an instant quote. An interactive application form allows you to select the coverage your business needs and make the policy payments.


How to file a claim with Huckleberry

The insurance carrier that Huckleberry matches you with will be in charge of determining the claims eligibility and payout by each assigned claims adjuster employed by it.



Huckleberry reviews: What customers are saying?


Consumers’ reviews for Huckleberry’s customer service agents are overwhelmingly positive, which is critical for the daunting obligation to have your business insured.



Source: Trustpilot



The verdict: Which small business insurance company should youi trust?  

Whether you’re a small business owner, a passionate entrepreneur or a large corporation, you need the right business insurance coverage, preferably one that helps you avoid unnecessary legal fees and worker’s compensation claims. However, selecting the right one for your situation depends entirely on the nature of your business and its requirements.


Next Insurance and Thimble offer a similar application process and quote claim in minutes, making it simple to purchase a policy, process a claim and obtain proof of insurance online – all without getting on the phone. Next Insurance, however, also offers email and phone support, along with recommended personalized policies, which is extremely helpful if you’re new to the insurance market or ever need to make any adjustments.


If the speed of claim resolution is your top priority, Next Insurance underwrites many of its own policies and manages its own claims, guaranteeing to resolve most claims within 48 hours. Thimble does not manage its own claims and may take additional time to resolve. Thus our #1 choice for most businesses is Next.


That said, Next Insurance exclusively offers monthly policies, while Thimble allows coverage options by the job, month or year. This is ideal for businesses in their early stages, giving them the option to potentially save early on and upgrade down the road. Thus Thimble is more nimble, and in some cases, may offer less expensive coverage.


Huckleberry works for small business owners who value the convenience and independence of online transactions and don’t mind working with an insurance broker (sans broker fee!). But business owners who purchase different kinds of coverage through Huckleberry may end up with more than one insurer, which might be slightly more difficult to manage. Thus while Huckleberry offers a lot of quality policies at an affordable rate, they are our third choice.


Which one of these small business insurance offerings would you try? Are you working with one currently? Let us know in the comments below!


Oh, and if all the talk about insurance has you wondering what other kinds of coverage you might want to buy online… check out our comparison of Hippo vs Lemonade, two leading online home insurance companies that can help you save a ton when insuring your home, apartment, and more! We’ve also reviewed Ethos vs Haven vs Ladder vs Bestow vs Fabric – a few of the best online life insurance companies


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About the Author

Alex Goldberg

Alex is a growth marketer, behavioral economics buff, and lover of all things Direct-to-Consumer. He enjoys scaling early-stage companies and working to bring transparency to opaque industries. He is a UC Berkeley grad, an aspiring retired golfer, and an avid soccer fan.

Learn more
Alex Goldberg

Alex Goldberg

Alex is a growth marketer, behavioral economics buff, and lover of all things Direct-to-Consumer. He enjoys scaling early-stage companies and working to bring transparency to opaque industries. He is a UC Berkeley grad, an aspiring retired golfer, and an avid soccer fan.

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