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Actuarial Director



United States
Posted on Thursday, July 27, 2023
About Us
Thimble is a leading insurtech platform for small business customers and agents. Thimble allows customers to quickly get insurance coverage by the job, month or year using its award-winning app, website, or over the phone.
Founded by serial entrepreneurs Jay Bregman and Eugene Hertz, Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents. Since it was founded, Thimble has delivered more than 170,000 policies to small businesses across the United States.
Thimble was acquired by Arch Insurance, a unit of Arch Capital Group Ltd. (Nasdaq: ACGL), a publicly listed Bermuda exempted company with approximately $15.6 billion in capital at Dec. 31, 2022. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.
Thimble's innovative culture and technical expertise are an incredible addition to Arch Capital’s portfolio of offerings. The acquisition expands Arch’s suite of digital solutions for small business customers and brokers. Thimble will remain a separate subsidiary, working closely with the Arch Group team.
For more information, visit thimble.com.
Our Values
Our unique culture is built around our six core values:
Think Wild, Act Tame
Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.
Green Means GO
Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.
Own Every Detail
Be ruthlessly precise. Disciplined. Sweat the small stuff.
Simplify, Simplify, Simplify
Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy – however hard that is for us.
Every Moment Counts
Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.
Stay Human
Treat every person, and their ideas, with respect. Cherish diversity.
About the Role
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.


  • 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 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

What We're Looking For

  • Bachelor’s Degree
  • FCAS highly preferred
  • 8+ 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)
  • Learn the data systems to allow for responses to data calls
  • Complete Claim Review & Analysis
  • 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, current strategic plan and OKRs, 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 development of/enhancement to commercial property insurance products
  • Assist in the development of new insurance products, including additional inland marine classes, excess liability, professional liability, and business auto product
  • Develop pricing and rating processes in coordination with the Product Team
  • Meet virtually with key partners for introductions
  • Streamline process for getting appropriate rates and rules into the system

What You’ll Do in 90 Days

  • Contribute to assure strategic projects and goals are on plan and suggest modifications, if required
  • Contribute to assure that the 2023-2024 Product Plan is on target and completed
  • Contribute to the plan for investigation of new products for 2023-2024 and beyond
Thimbler Benefits & Perks
-Fully remote company
-Thimble Fridays! (out of office at 12:00pm local time)
-Comprehensive health, vision, and dental coverage
-PTO: 20 days vacation, 8 floating days, 10 company-wide holidays, 1 VTO (Volunteer Time Off), and unlimited sick time
-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return
-Company computer hardware of your choice
-Work from home setup reimbursement
-Monthly co-working space and/or child care reimbursement
-Monthly ClassPass credit
-Quarterly wellness reimbursement
-Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
-Virtual events, happy hours, trivia, and fun!