Companies you'll love to work for

Licensed Insurance Customer Service Representative (East or Central Region)



Customer Service
United States
Posted on Tuesday, July 2, 2024
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
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
Thimble is seeking a motivated Customer Service Representative to add to our team, located in either the East Coast or Central time zone. In this role, you will work closely with other team members to provide outstanding service to our customers by answering questions, handling complaints, and troubleshooting problems with our products and services. This role also includes assisting prospective customers with quoting and binding policies on our platform.
The Customer Service Representative may handle a high volume of calls, chats, and emails, and should seek to create a positive experience for each customer. They will listen to clients to understand the reason for their support request, address all questions or complaints, and provide an accurate and efficient response. This is a unique role that will require determination to help enhance the Customer Service function at a quickly growing start-up.


  • Assist new and existing customers through all of their inquiries and help them find a resolution to any questions or issues that they may have.
  • Help increase conversion by bringing valued product and insurance knowledge to the purchase experience for new customers.
  • Aid existing customers with policy modifications and examine coverage options.
  • Meet defined Service Level Agreements for assisting new and existing customers with service requests.
  • Provide excellent customer support and assistance via phone, email, and chat.
  • Dedicated to helping the customer succeed at all costs; you are the front line between the customer and Thimble, we want to leave a positive impression and develop a relationship that keeps the customer happy.

What We're Looking For

  • A Property & Casualty Insurance license is required. Small commercial business insurance experience highly preferred.
  • Experience in a fast-paced, high-volume support environment.
  • Flexible and willing to work with all teams in the company to meet our values.
  • Excellent written and oral communication skills.
  • Highly organized with ruthless attention to detail.
  • Ability to adapt to changes and learn quickly.
  • Bachelor’s degree or equivalent experience required.

What You’ll Do in 30 Days

  • Get a warm welcome, meet the rest of the company, and get situated in your new position.
  • Gain a thorough understanding of our insurance product offerings, all of the nuances of the policy, and the different channels and ways that we sell coverage.
  • Become familiar with our various software (Zendesk, Looker, Asana, Stripe, KwikComply & more)
  • Begin answering phone calls, taking support tickets and chats, and getting a pulse for Thimble’s customer base.

What You’ll Do in 60 Days

  • Be completely comfortable with our suite of products and offerings.
  • Be able to answer standard tickets, chats, and calls within defined SLA’s.

What You’ll Do in 90 Days

  • Full end-to-end product knowledge.
  • Have complete ownership of your area of customer service and be fully skilled in phone support. email, chat.
  • Assist other members of the company with product/underwriting inquiries.
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!