Episode 40: On Changing how Small Businesses Think about Buying Insurance with Jay Bregman, CEO & Founder of Thimble

On this week’s episode of Subscriptions: Scaled, we speak with Jay Bregman, CEO & Founder of Thimble. 

Thimble offers insurance tailored to businesses, allowing organizations to purchase insurance online with policies by the hour, day, week, or month. The brand sets out to change the way small business owners think about buying insurance.

In the episode, we learn how Thimble is changing how brands think about buying insurance. Please keep reading to learn all about Jay’s background in the industry and more about Thimble and how its subscription-based model works.

Thimble

Before Thimble, businesses were forced to purchase insurance policies they couldn’t afford, didn’t need, and probably didn’t understand. But using Thimble, a subscription-based model that can be bought and managed using the brand’s app, small businesses can choose affordable insurance that is easy to understand and manage and covers the necessities.

Thimble covers all types of businesses, including handypersons, landscapers, DJs, and more. Companies can arrange insurance as and when they need it, getting covered instantly if necessary.

Businesses can buy a policy online, in the app, or over the phone in mere minutes. Plus, insurance is available for any size company at any stage.

Coverage is available by the job, month, or year, making it completely flexible. Businesses can also choose how they pay and can upgrade their insurance policies when their company takes off. 

There are no hidden fees, and businesses can modify, pause, or cancel their insurance instantly—whether hiring picks up, or if work slows. 

Thimble has several awards under its belt, too. The brand made MONEY Magazine’s 2021 “Best Insurance for Small Businesses” and became Fast Company’s #1 “Small and Mighty” Company. 

The reviews are glowing, too. Thimble is rated 4.8 out of 5 stars in Trustpilot and the App Store. Since its establishment, Thimble has sold more than 125,000 policies to over 40,000 small businesses.

Thimble offers different types of coverage, including drone insurance, a relatively new kind of insurance for businesses to invest in.

How Thimble Was Established

Jay begins the podcast by explaining his background and how the concept for Thimble came about and grew. Jay has started three businesses in his career, the last being a ride-sharing company in London called Halo. The company was sold to German multinational automotive corporation Daimler a couple of years ago.

One of the things Jay noticed after establishing Halo was how small businesses were being created and were developing in new ways with the help of technology—particularly mobile technology. Customers were interested in using transactional, easy-to-use mobile businesses rather than walking into shop fronts or signing up to companies with plenty of paperwork.

Jay then started thinking about small businesses and how they were signing up to manual, annual insurance policies. He realized there needed to be a fundamental change in business insurance. So Jay sought out to change the business insurance market.

With a friend of his, Eugene Hertz, he established Thimble with the idea of changing the future of the insurance industry. They built the Thimble platform so customers could buy and manage business insurance using an app to cover everything they wanted by answering just three questions.

All the unnecessary underwriting questions that most people are used to when buying insurance were removed. Instead, they distilled the questions down to the few that were necessary. 

Jay and his partner created a system for attracting the modern small business owner. Approximately 70 percent of Thimble’s customers had never taken out business insurance before, and 54 percent started their company within the last three years. About 30 percent of Thimble’s policies are also purchased using the app. Then, 42 percent of customers who bought went to download the app to help them manage their policies.

With Thimble, businesses can purchase insurance simply and easily.

What Makes Thimble Special

Jay goes on to share what makes Thimble so unique and how it stands out from other small business insurance companies. 

Thimble offers a streamlined and high-quality experience for customers on the app, with plenty of features that make purchasing and managing insurance easy. Thimble provides a pause feature so people can pause their policies as and when they please.

When potential customers check out Thimble, they can see plenty of great features, including the pause feature, instant cancellation, and no annual commitment. Many people see that they don’t have to worry about getting locked into a policy as they usually would with insurance plans and find the model attractive. As the policies are customizable and can be easily managed, people often see them as their own policies that they’re in control of.

We also learn how Thimble educates people on its business model, showing them a new way to procure insurance.

API Integrations

In the episode, we also discover how API integrations are beneficial for Thimble. As Thimble is a service that’s easy to use, it only has a couple of questions for customers to answer, and everything can be managed programmatically.

Thimble embeds onto companies like Angie’s List or Peerspace, expanding its reach and distributing its services that way. 

Jay sees embedded insurance as the future and, as such, is investing very heavily in it.

The Target Customer

While Thimble wants to target all types of small business, there are some that are particularly interested in using the brand. 

Some popular businesses signed up to Thimble include handypersons, contractors, and home repair companies. These are typically businesses that require insurance, but their industries have been left behind by technology. They’re technological business owners, but they don’t have technical solutions that are typically tailored to them or work for them.

There are also many photographers using Thimble, people that are constantly on the go and working on shoots. 

However, all-in-all, Thimble’s customer base is a very diverse selection of businesses that represent the economy, which was Jay’s aim for the company.

The Future of Thimble

The episode wraps up with Jay sharing the future goals of Thimble. He expects there to be more types of coverage all available on the same platform offered today, aiming to perfect the user experience.

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