Job Details

  • Full Time
  • Fully Remote
  • Posted:

Actuarial 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 an Actuarial Director to lead Thimble in the development, implementation, and offering of new insurance products to a wider and more diverse customer base, and to own the pricing of our insurance products across our organization.

Role and Responsibilities

  • Primary actuarial support for Thimble Insurance Services, our general agency.
  • Provide leadership, vision, and direction to:
    • Drive pricing decisions including the advancement and execution of pricing tools and trend analyses. Work closely and cross-functionally with the Product Team which has responsibility for implementation of products and the User Experience across our app, web, APIs, and broker platforms.
    • Mastermind pricing of new products and coverages, including cutting-edge products with limited or no historical experience, performance monitoring, and trend analysis.
    • Work with the Leadership Team and the Finance Team, to play a key role in the production of the Thimble Operating Plan.
    • Propose and introduce changes or improvements that promote profitability and growth and take an active role in the implementation of these changes including defense to state regulators and reinsurers.
    • Communicate results analysis and recommendations in a manner that is understandable and allows management to make operational changes where necessary with efficacy.
    • Provide strategic and operational planning advice including monthly and quarterly reporting to the Leadership Team, assessment of profit and financial performance, and front-line risk management for Thimble business segments.
    • Develop and defend filings for regulators and defend them to regulators and capital partners.
    • Develop materials /reports for insurance and reinsurance risk capital partners and regulators.
    • Represent Thimble to underwriting executives and senior actuaries at various partner organizations.
    • Be relentlessly creative in the pursuit of new ways of pricing and structuring risk products for modern businesses.


  • Bachelor’s Degree.
  • FCAS or strong actuarial background required. 10+ years insurance P&C experience with at least 5 years’ experience in commercial lines.
  • Proactive individual who challenges existing processes, can influence others (including regulators) and drive a process to conclusions while meeting critical deadlines.
  • Independent thinker as well as challenger/advocate ensuring soundness of pricing and underwriting.
  • Drive to deliver results and strive for continuous improvement.
  • 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, thinking and acting strategically, planning for the long-term while balancing short-term needs of the organization.
  • Exceptional written and oral communication skills.
  • Creative problem solving, organizational, and planning skills.
  • Exceptional analytical and critical thinking skills with ruthless attention to detail.

What You’ll Do in 30 Days:

  • Understand Thimble’s product set and roadmap.
  • Take ownership of Thimble’s pricing initiatives.
  • Complete Pricing Review & Analysis (Delta from Current Filing and Justification for Competitive Positioning).
  • 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 and reinsurer guidelines as they have been presented to us.
  • Carrier Partner pricing and rate/rule filing work 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 the development of event offerings in the GL and IM LOBs.
  • Assist in the development of commercial property insurance products.
  • Assist in the development of automobile insurance products, including hired/non-owned auto products.
  • Develop pricing and rating processes in coordination with Product Team.
  • Meet virtually with key partners for introductions.
  • Streamline process for getting appropriate rates and rules into system.

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 pricing of 3rd Party Cyber product offering.
  • Assist in pricing 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.