Jobs and Careers
TH
Insurance Operations Specialist (Small Commercial Insurance - All Lines)
ThimbleUnited States, United StatesRemotefull_timeVerifiedPosted 1 May 2025
About the role
About UsThimble 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 entrepreneur Jay Bregman, 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 ValuesOur unique culture is built around our six core values:
Think Wild, Act TameBe 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 GOAct. Move forward. Learn. You can only make a decision based on the best information you have – so make it.
Own Every DetailBe ruthlessly precise. Disciplined. Sweat the small stuff.
Simplify,Simplify, SimplifyGet 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 CountsShow up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.
Stay HumanTreat every person, and their ideas, with respect. Cherish diversity.
OverviewWe are seeking an Insurance Operations Specialist to provide support to the Insurance Team of Thimble, the industry's compliant radicals, in the risk selection and review of the current book as well as the implementation and offering of new products to a wider and more diverse customer base.
Role and Responsibilities Primary Insurance Operations Specialist responsibilities for the Verifly Insurance Services, LLC dba Thimble Insurance Services, a general agency, to include the following:
--Assist in the 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 members of the Insurance Team where required --Assist in the preparation 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 --Support the monitoring of and management of Thimble's underwriting risk to deliver target loss ratio while supporting Thimble's mission and strategy --Provide support for making necessary underwriting changes --Assist in the preparation and delivery of regulatory notices to insureds --Support the Insurance Team with the building of requirements for changes to Thimble's customer and broker quote flow, appetite, or form updates
Founded by serial entrepreneur Jay Bregman, 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 ValuesOur unique culture is built around our six core values:
Think Wild, Act TameBe 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 GOAct. Move forward. Learn. You can only make a decision based on the best information you have – so make it.
Own Every DetailBe ruthlessly precise. Disciplined. Sweat the small stuff.
Simplify,
Every Moment CountsShow up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.
Stay HumanTreat every person, and their ideas, with respect. Cherish diversity.
OverviewWe are seeking an Insurance Operations Specialist to provide support to the Insurance Team of Thimble, the industry's compliant radicals, in the risk selection and review of the current book as well as the implementation and offering of new products to a wider and more diverse customer base.
Role and Responsibilities Primary Insurance Operations Specialist responsibilities for the Verifly Insurance Services, LLC dba Thimble Insurance Services, a general agency, to include the following:
--Assist in the 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 members of the Insurance Team where required --Assist in the preparation 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 --Support the monitoring of and management of Thimble's underwriting risk to deliver target loss ratio while supporting Thimble's mission and strategy --Provide support for making necessary underwriting changes --Assist in the preparation and delivery of regulatory notices to insureds --Support the Insurance Team with the building of requirements for changes to Thimble's customer and broker quote flow, appetite, or form updates
What We're Looking For
- 5+ years of experience in the P&C segment, including small commercial experience
- Ability to analyze and make decisions quickly and decisively
- Insurtech and/or startup experience highly preferred
- 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
- Exceptional written and oral communication skills
- Microsoft Word and Excel proficiency
- Creative problem solving, not problem identifying
- Experience with a digital underwriting platform preferred
- Bachelor's Degree or equivalent experience
What You'll Do in 30 Days
- Understand Thimble's product set and roadmap
- Take ownership of Thimble's Insurance Ope
Apply for this role
Generate a tailored application kit with a matched cover letter, interview prep, and CV highlights — in under 60 seconds.
Apply Now →Generate Application KitFree account required — sign up in 30s