Job Details

  • Full Time
  • Remote
  • Posted:

Customer Success Representative

About Thimble

Thimble’s mission is to make insurance simple, to help businesses succeed on their own terms. To do this, we’ve built a new insurance stack – from the ground up – designed to tackle the uncertainty of starting, running, and growing a modern business.

How does it work? Answer three simple questions and we instantly deliver a certificate of liability insurance straight to your phone. Available as a monthly subscription or tailored to a single job, Thimble is designed to fit your business and seamlessly grow with your ambitions. You won’t need to call us because you’re always in control: scale-up, modify, and even pause or cancel your policy with a single tap.

Thimble is one of the fastest-growing small business insurance services in America. We’ve sold over 135,000 policies representing over $150B in coverage since launching in 2016. Over 1,000 customers have rated our apps with an average of 4.8-stars. honored Thimble as the Best Business Insurance for 2020.

Founded by three-time entrepreneurs Jay Bregman and Eugene Hertz, Thimble is a remote-first company based in New York City. We’ve raised $30 million in funding from IAC (NASDAQ: IAC), Slow Ventures, and other top firms. For more information, visit or search “Thimble” on the App Stores.


Thimble is seeking a motivated Customer Success Representative within our Operations team to scale our evolving Customer Support and Sales function. You will help new and existing customers via email, chat, and our newly launched phone lines. This is a unique role that will require determination to help enhance the Customer Service function at a fast-growing start-up. In this role, you will work with all teams within the company, providing customer feedback to help shape decisions across Product, UX, Marketing, and Business Development teams.

Roles and Responsibilities

  • Assist new customers in determining whether Thimble is a fit for them and assist them through their policy purchase.
  • 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 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.


  • A Property & Casualty Insurance license is required
  • 1-5 years of experience in a Customers Sales / Support function
  • Ability to work effectively and efficiently in a remote environment
  • 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

In 30 days, you will…

  • 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: Freshdesk, Freshchat, 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!

In 60 days, you will…

  • 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.

In 90 days, you will…

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


  • Comprehensive health, vision, and dental coverage.
  • 20 days paid vacation plus company-wide holidays.
  • Ability to work remotely bar 1-2 days per month onsite meetings in New York City.
  • Company computer hardware of your choice and a generous contribution to your remote office.
  • Virtual trivia and field trips.
  • Competitive pay.
  • Generous stock options.

*No recruiters please*

How to apply