Job Details

  • Full Time
  • Fully Remote
  • Posted:

Underwriting Compliance Director

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 125,000 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.


We are seeking Underwriting/Compliance Director to lead Thimble in the development, implementation, and offering of new products to a wider and more diverse customer base.

Role and Responsibilities

  • Primary underwriting responsibilities for Thimble Insurance Services, a general agency, to include the following:
    • Ongoing development, revisions, 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.
    • Liaising with insurers represented by Thimble.
    • Assist claim adjusters with underwriting issues on claims, where required.
    • Liaising with Departments of Insurance
  • Responsibility for compliance reviews of policy forms, underwriting guidelines, practices and processes used by Thimble.
  • Coordination of audits by insurers, reinsurers and regulators.
  • Develop and drive initial filings for new products and filing updates for mature products that do the following:
    • Contain meaningfully unique features highly valuable to our customers.
    • 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 insurance industry experience in P&C underwriting and compliance.
  • Ability to work well and respectfully with others, with minimal supervision 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.
  • Creative problem solving, not problem identifying.
  • Bachelor’s Degree.

What you’ll do in 30 days:

  • Understand Thimble’s product set and roadmap.
  • Take ownership of Thimble’s underwriting process.
  • Understand Thimble’s Parametric BI offering.
  • 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.
  • Understand organization, 2020 plan, and the insurance challenges.
  • Understand Carrier guidelines as they have been presented to us.
  • Carrier Partner Compliance Reviews for four lines of business.

What you’ll do in 60 days:

  • Understand Thimble’s financial model and insurance impact/budget.
  • Understand Thimble’s Business Development strategy (especially broker strategy) and impact of Thimble’s Business Development on insurance roadmap.
  • Assist in development of commercial property insurance product.
  • Assist in the development of automobile insurance products, including hired/non-owned auto product.
  • Develop compliance review process in coordination with Product Team.
  • Meet virtually with key partners for introductions.
  • Support Product and Marketing Teams in development and revisions of content-driven purchase experience.
  • Streamline the process for getting appropriate forms into our systems.

What you’ll do in 90 days:

  • Contribute to assuring strategic projects and goals are on plan and suggest modifications, if required.
  • Contribute to assuring that the 2020 Product Plan is on target and completed.
  • Contribute to planning for investigation of new products for 2021-2022 and beyond.
  • Assist in the development of 3rd Party Cyber product offering.
  • Assist in the development of Workers Compensation product offering.

Benefits and Company Culture

  • Comprehensive health, vision, and dental coverage.
  • 20 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.

How to apply

Click here to apply for this position.  No recruiters.