The Thimble Certificate Manager

The only 100% free Compliance Manager to get the right insurance, from the right people, the first time.


Thimble sells flexible, short-term business insurance for the gig economy, with policies available by the hour, day, or week, up to a full year for growing businesses reaching the next level. Policies can be purchased in seconds via the web or app, with the ability to modify, pause, or cancel instantly whether work slows down or hiring picks up. This innovative product-offering in a truly archaic industry earned Thimble the 1st place spot on Fast Company’s Most Innovative Companies, in the "Small and Mighty" category.

Project Background

The Thimble Certificate Manager was my first true passion project, starting with a single data point and evolving into an entirely new platform and market for Thimble. While performing some data analysis, I uncovered that 40% of our customers purchased insurance solely because they were required to by their clients. This was evident through the concept of “Additional Insureds,” a document where a policyholder lists the businesses they work for, which extends insurance coverage to the business.

To my surprise, companies like Marriott Hotels, Netflix, Airbnb, and SXSW were frequently listed as Additional Insureds on Thimble policies. It was apparent that these companies were hiring freelancers and contractors, our core market, and requiring them to have insurance. Notably, 85% of Thimble's customers were first-time insurance buyers (this data is documented in our 2019 Gig Economy Report, another Project I worked on).

I saw an opportunity to create a solution that would encourage these companies to direct their freelancers to Thimble, and the Thimble Certificate Manager was born.

Watch the promotional video created by the great Garrett Mireles and I.

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The Thimble Certificate Manager acquired over 2,000 customers at a $0 Acquisition Cost over its first six months, including 500 customers in a 2-week span via a SXSW Partnership in 2022.


I wanted to learn the process of hiring and approving contractors to see if Thimble could fit somewhere in that process. I was able to connect with some of the organizations listed on Thimble policies, including Goldenvoice, SXSW, and a lovely Real-Estate Photography company called Virtuance. Each contact walked me through the process of hiring and approving contractors:

  1. The organization shares insurance requirements via a PDF, Email, or Phone Call. These requirements tend to be incredibly specific.
  2. If the contractor has a policy, they make the necessary changes by calling their broker. If they don't, they do some googling and hope to find a policy that meets each requirement.
  3. The contractor sends their Policy (a "Certificate of Insurance") to the Organization to be reviewed.
  4. More often than not, some or all of the requirements are missing. My research showed that only 20% of policies were correct the first time.
  5. The organization and the contractor go back and forth until everything is resolved. Once everything is approved, the Organization keeps track of the contract and policy duration, to make sure there's not a single second where the contractor is working uninsured (this is usually managed through a spreadsheet).

Most of this reviewal process happens in E-Mail Chains, spreadsheets, and highlighting actual PDFs! Approving contractors for work while limiting risk is an ongoing struggle throughout multiple industries. Studies show that property managers spend up to 10% of their time collecting Certificate's, waiting for changes, and verifying renewals. Some corporations are beginning to move to a digital process, but at an incredibly high cost that small businesses cannot afford.

There was obviously a better way to do this.

A birds eye view of all your contractors. Contractors who buy a policy from Thimble are auto-approved, so you don't even have to review the PDF!

The Solution

I set out to develop the Thimble Certificate Manager- the only 100% free Compliance Manager for requesting, approving, and managing your contractors insurance. I gave my presentation to Thimble's Co-Founders, and was given 3 months and 4 engineers to build the Certificate Manager. I was responsible for designing the product, managing development end to end, developing a go-to-market strategy, settings targets and defining success.

Key features include:

  • Automated communications - Hassle-proof automated emails and reminders to contractors
  • Easy COI Reader - Key information extracted from Certificates of Insurance, side by side with your requirements
  • Policy status dashboard - A bird’s eye view of who’s working where, with expiration notifications
  • Manage any Policy - Contractors can purchase a policy from Thimble, or upload their own. Already have documents for freelancers under contract? Upload them now, and we'll alert you when they're expiring.
  • Best of all, Auto-approved policies - Policies for contractors sold directly by Thimble, guaranteed to meet your requirements


We used to face problems with certificates expiring or being cancelled without our knowledge. The Thimble Certificate Manager had many of the features we were looking for without spending thousands of dollars.

- Janelle Matejcek, Virtuance

Landing page for the contractor that is working for the Certificate Manager User- who has the option to buy a pre-built policy from Thimble, or upload their own policy.

By offering a free compliance manager to these companies, every contractor hired by an organization using the Certificate Manager becomes a lead. And not just any lead, these contractors are actively being requested to provide proof of insurance in order to start work, making them incredibly qualified leads.

Not only is Thimble the only short-term insurance provider, but buying your policy through Thimble removes the headache of getting approved for work, making Thimble the obvious choice for un-insured contractors. Even contractors who upload their own policies become qualified leads in the days before their policy expires (and Thimble has their email and Policy expiration date 😎).

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When I left Thimble in 2022, the Certificate Manager had acquired over 1,000 organizations, with 30% of organizations referring a customer to Thimble in their first 7 days. It was a self-sustaining Channel acquiring customers at a $0 Customer Acquisition Cost, growing 80% MoM.

Go to Market

Thimble was essentially sitting on a robust marketing strategy, just waiting to be turned on. As we sold policies direct-to-consumer, 40% of them would add an Additional Insured. All we had to do was contact those Additional Insureds and sell them on our free product. I made the decision to start requiring e-mail address for every Additional Insured. When an Additional Insured is added to a Thimble Policy, they enter a drip campaign where we provide the Certificate of Insurance and advertise the Certificate Manager. Believe it or not, an automated email in our 2nd month landed us the SXSW partnership.

We did bump into some activation struggles, finding it difficult to educate organizations about the product. Many of these companies hadn't heard of a digital Certificate Manager, and didn't full understand the features. I decided to push these Organizations directly into the funnel- updating our flow so Certificates of Insurance were only available in the Certificate Manager, sending Additional Insureds to a "Logged Out" view of the Certificate Manager. In this logged out view, you can review the details of the policy in a friendly UI (the COI Easy-Reader), request changes, set an alarm for expirations, and more. This new flow boosted signups and activation by over 30%.

Additional Insured CRM: When an organization is added to a new or existing policy, we alert them via email and drive them to a Logged Out version of the Certificate Manager in order to see the Certificate of Insurance.

The Logged Out Certificate Manager lets you review the limits, endorsements, dates, and more in a user-friendly UI rather than combing through a 20 page PDF. It has features to request changes, set alerts for expirations, and more. You can even use this policy to create your first Project, and request other contractors to have the exact same policy.

Since launch, transactions attributed to Certificate Manager users have been growing at an average rate of 80%.