Thimble Licensed Customer Success Representative

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, 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 $24.3 billion in capital at March 31, 2025. 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 

Thimble is seeking a motivated Customer Success Representative to add to our team, located on the East Coast (EST time zone). In this role, you will 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 insurance and underwriting questions related to our appetite and binding policies on our platform.  

The ideal Customer Service Representative can handle a high volume of emails and chats, and seeks to create a positive experience for each customer. Listening to clients to understand the reason for their support request, addressing all questions or complaints, and providing accurate and efficient responses are all key parts of success for this role. 

Please note: Thimble Fridays benefit (out of office at 12:00pm local time) is subject to a different day for the Success Team.

• Assist new and existing customers through all of their inquiries and help them find a resolution to any questions or issues they may have. 
• Help increase conversion by bringing valued product and insurance knowledge to the purchase experience for new customers.  
• Work with internal teams by providing customer success feedback and user experience data.   
• 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 email, chat, and phone. 
• 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.   
• Assist with side projects as needed for the insurance and product teams. 

• An active 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 preferred 

• Get a warm welcome, meet the rest of the CS team and 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 and systems (Zendesk, Confluence, Stripe, Omni, Jira, KwikComply + more)  
• Begin taking support tickets and chats, and getting a pulse for Thimble’s customer base.  

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

• Full end-to-end product knowledge. 
• Have complete ownership of your area of customer service and be fully skilled in support via email and 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

-401(k) auto enrollment and matching (100% of the first 3% and 50% of the next 3%)

-PTO: 20 days vacation + 12 company-wide holidays + 8 floating days + 1 VTO (Volunteer Time Off) + unlimited sick time

-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return

-Computer choice of Mac or PC

-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!