Insurance /Full Time /Remote

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

We are hiring a Broker Success Associate in the East Region to assist with broker sales support, including new broker onboarding and ongoing broker relationships. This role is dedicated to helping drive results for the broker team at Thimble. The broker success team provides training and support to producers to help them adopt the company's products and services effectively as well as follow broker success plans to ensure that producers achieve their desired outcomes.

To succeed in this role, you should have excellent communication and interpersonal skills and will quickly learn to understand the company's products and services. You should also be highly organized, professional, and able to manage multiple projects simultaneously.

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

Roles and Responsibilities

Become an expert with Thimble’s products and services
Be the front line between the broker and Thimble. We want to leave a positive impression and develop a relationship that keeps the broker happy
Provide brokers with timely and solution‐oriented responses to their business needs
Provide overall excellent broker support and assistance, mainly through a high volume of tickets and chats
Support the onboarding process for new brokers while delivering excellent customer service
Provide guidance and best practices on configuring and utilizing the Thimble Broker Portal
Help increase activation by bringing valued product and insurance knowledge to the purchase and servicing experience for new brokers
Work closely with Customer Success and the Insurance team to remain aligned on compliance
Collaborate with other teams to provide feedback on broker and user experiences

What We’re Looking For

A Property & Casualty Insurance license is required
Commercial insurance experience is required; small commercial business insurance experience is highly preferred
Prior work with insurance brokers or agencies
Experience in a fast-paced, high-volume support or customer service environment
Excellent written and oral communication skills
Highly organized with ruthless attention to detail
Ability to adapt to changes and learn quickly
Ability to manage multiple projects simultaneously

What You’ll Do in 30 Days

Meet the team and gain a thorough understanding of our insurance product offerings, policies, different channels, and the ways that we sell coverage
Shadow and train with the Broker Success and Customer Success teams
Become familiar with our various software (Zendesk, Omni, Jira, and more)
Learn Thimble’s broker base and become comfortable answering various tickets

What You’ll Do in 60 Days

Be completely comfortable with our suite of products and offerings
Be able to receive and respond to most broker tickets with support from the Broker Success team

What You’ll Do in 90 Days

Full end-to-end product knowledge
Have complete ownership of your area of broker development and answering tickets
Be integrated with other teams and collaborate on Thimble’s projects

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!

Thimble jobs

(East Region) Commercial P&C Support Representative