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. \n Responsibilities 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

What We're Looking For 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 What You’ll Do in 30 Days 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

What You’ll Do in 60 Days Be completely comfortable with our suite of products and offerings

Be able to answer standard tickets and chats 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 support via email and chat.  Assist other members of the company with product/underwriting inquiries. \n 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!