Job Details

  • Full Time
  • United States
  • Posted:

Customer Sales Representative (Commercial Insurance)


Thimble is seeking a motivated Customer Sales Representative to help scale our quickly evolving Customer Sales team. In this role, you will work closely with our team members to provide outstanding sales and customer support by guiding our clients through the important steps of purchasing coverage they need for their modern business.

The Customer Sales Representative will handle a high volume of inbound or outbound calls seeking to create a positive experience for each customer. This person will answer questions from the clients, offer additional products applicable to their business, all with the objective of acquiring that client as a customer. This is a sales-focused role that will require determination and drive to grow this important function at a quickly growing start-up. This role will report to the Senior Vice President of Business Development, and will have the opportunity to learn and grow in a number of areas including general sales acumen, consultative selling, technical insurance terms and coverage.

Roles and Responsibilities

  • Inbound and Outbound sales responsibilities originating from direct to consumer marketing efforts and partner leads focused on the Small Business sector across the US
  • Assist prospective and new customers through all of their inquiries to help them find a resolution through existing insurance products
  • Help increase conversion by bringing valued product and insurance knowledge to the purchase experience for new customers
  • Meet defined Sales objectives for assisting new and existing customers with service requests
  • 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 license is required
  • 2+ years of experience in a customer sales/business development or support function
  • Commercial insurance experience
  • Flexible and willing to work with all teams in the company to meet our values
  • Driven to provide guidance to prospective and existing clients
  • Highly motivated, driven sales individual
  • Bachelor’s degree or equivalent experience

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 Thimble’s insurance product offerings, and the different channels from which we attract customers to Thimble
  • Become familiar with our various software tools: Zendesk, Looker, Whimsical, Asana
  • Begin handling inbound and outbound sales calls to prospective clients
  • Work with our Customer Success team on how best to service our customers through the different types of interactions with our clients
  • Work with the Customer Success Manager and the head of Business Development to see how it’s done!

What You’ll Do in 60 Days:

  • Be completely comfortable with our suite of insurance products and offerings
  • Identify areas of improvement in our Customer Sales function through analytics to help shape customer sales strategies throughout the company
  • Assist in Customer Sales reporting, defining sales and performance metrics, and meeting them with rigor

What You’ll Do in 90 Days:

  • Have complete ownership of your area of customer sales and be fully skilled in inbound / outbound sales functions and responsibilities
  • Full end to end product knowledge
  • Assist other members of the company with sales support 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 Sales Representative