Job Details

  • Full Time
  • Remote
  • Posted:


About Thimble

Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. To do this, we’ve built a new insurance stack – from the ground up – designed to tackle the uncertainty of starting, running, and growing a modern business.

How does it work? Answer three simple questions and we instantly deliver a certificate of liability insurance straight to your phone. Available as a monthly subscription or tailored to a single job, Thimble is designed to fit your business and seamlessly grow with your ambitions. You won’t need to call us because you’re always in control: scale-up, modify, and even pause or cancel your policy with a single tap.

Thimble is one of the fastest-growing small business insurance services in America. We’ve sold over 135,000 policies representing over $150B in coverage since launching in 2016. Over 1,000 customers have rated our apps with an average of 4.8-stars. honored Thimble as the Best Business Insurance for 2020.

Founded by three-time entrepreneurs Jay Bregman and Eugene Hertz, Thimble is a remote-first company based in New York City. We’ve raised $30 million in funding from IAC (NASDAQ: IAC), Slow Ventures, and other top firms. For more information, visit or search “Thimble” on the App Stores.

Role and Responsibilities:

  • Primary underwriting responsibilities for the Verifly Insurance Services, Inc. dba Thimble Insurance Services, a general agency, to include the following:
    • Ongoing development, revision, implementation, and maintenance of underwriting guidelines and coverage applications
    • Ensure adherence to underwriting guidelines and principles of Thimble
    • Underwriting referrals in accordance with Thimble standards
    • Assist claim adjusters with underwriting issues on claims where required
  • Assist in the development of initial filings for new products and filing updates for mature products that do the following:
    • Contain meaningfully unique features perceived highly valuable by our customer groups
    • Allow Thimble to grow significantly in the SMB market
    • Solve the basic insurance needs of our customer groups
    • Produce an acceptable underwriting profit
  • Monitor and manage Thimble’s underwriting risk to deliver target loss ratio while supporting Thimble’s mission and strategy
  • Identify necessary underwriting changes


  • 15+ years of insurance industry experience in P&C underwriting
  • Ability to work well and respectfully with others, with minimal supervisions, and in a very fast-paced environment
  • Ability to effectively manage multiple projects, prioritizing high impact ones
  • Ability to make decisions quickly and decisively
  • Exceptional written and oral communication skills
  • Microsoft Word and Excel proficiency
  • Creative problem solving, not problem identifying
  • Bachelor’s Degree

Within 30 days, you will:

  • Understand Thimble’s product set and roadmap
  • Take ownership of Thimble’s underwriting process
  • Understand Thimble’s content/SEO strategy and the Insurance team’s role in it
  • Understand Thimble’s designated producer strategy
  • Digest company performance and customer data to date and training on Thimble’s data infrastructure
  • Review data dump including all team presentations, Board presentations, filings, PAA agreements, carrier presentations, and product documentation
  • Understand Thimble’s claims process and future plans
  • Understand organization, 2021 plan, and the insurance challenges
  • Understand Carrier guidelines as they have been presented to us

Within 60 days, you will:

  • Understand Thimble’s financial model and insurance impact/budget
  • Understand Thimble’s Business Development strategy, including broker strategy and impact of Thimble’s Business Development on insurance roadmap
  • Assist in the development of commercial property insurance product
  • Assist in the development of automobile insurance products, including hired/non-owned auto product

Within 90 days you will:

  • Contribute to assuring strategic projects and goals are on plan and suggest modifications, if required
  • Contribute to assuring that the 2021 Product Plan is on target and completed
  • Contribute to planning for investigation of new products for 2022-2023 and beyond


  • Comprehensive health, vision, and dental coverage.
  • 23 days paid vacation plus company-wide holidays.
  • Ability to work remotely bar 1-2 days per month onsite meetings in New York City.
  • Company computer hardware of your choice and a generous contribution to your remote office.
  • Virtual trivia and field trips.
  • Competitive pay.
  • Generous stock options.

**No recruiters please**

How to apply