Job Details

  • Full Time
  • United States
  • Posted:

Customer Success Representative



Thimble is seeking a motivated Customer Success Representative within our Operations team to help scale our quickly evolving Customer Support function. 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. The Customer Service Representative may handle a high volume of inbound or outbound calls and should seek to create a positive experience for each customer. They will listen to clients to understand the reason for their call, 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.


Roles and Responsibilities


  • Work on our newly launched phone support operation by taking incoming calls from prospective and existing customers.
  • 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 on policy modifications and examining 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.




  • A Property & Casualty Insurance license is required
  • 1-2 years of experience in a Customers Sales / Support function
  • Flexible and willing to work with all teams in the company to meet our values
  • Excellent written and oral communications skills
  • Highly organized with ruthless attention to detail
  • 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 softwares: Zendesk, Looker, Whimsical, Asana, Stripe, KwikComply and more.
  • Begin answering support tickets and chats and getting a pulse for Thimble’s customer base.
  • Shadow our Customer Success Manager and see how it’s done!


What You’ll Do in 60 Days:


  • Be completely comfortable with our suite of products and offerings.
  • Identify areas of improvement in our Customer Support function through analytics to help shape product decisions throughout the company.
  • Assist in Customer Support reporting, defining Service Level Agreements, and meeting them with rigor.


What You’ll Do in 90 Days:


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




  • Comprehensive health, vision, and dental coverage.
  • 23 days paid vacation plus company-wide holidays.
  • Ability to work remotely.
  • Company computer hardware of your choice and a generous contribution to your remote office.
  • Virtual trivia and field trips.
  • Competitive pay.
  • Generous stock options.


How to apply

Apply Here for Customer Success Representative