Two Chicks With A Side Hustle

Employer: Cover Whale

Who is Cover Whale?

Cover Whale employs data to make our roads safer – and we’re looking for exceptional humans to help us make our vision a reality. Our ambition is to combine our passion for improving safety with leading expertise in data science, along with industry leading practices in AI/ML/FL to not only identify good driver, but to actually make our drivers and the roads they travel safer. We realize that the commercial trucking industry is the backbone of the American supply chain; here at Cover Whale, our goal is to drive progress in the trucking industry by providing innovative, dynamic insurance solutions that open new horizons of possibilities to drivers, fleet owners, and everyone in between.

Founded in 2019, Cover Whale recently closed a $15.5M seed funding round (the largest InsurTech seed round raised in North America to date), and is scaling rapidly. Cover Whale was built on a foundation of technology, data, and machine learning analytics to transform the commercial auto segment and bring the excitement of consumer insurance tools like Lemonade and Hippo to the commercial auto space. The efficiency driven by Cover Whale’s technology platform reduces the need for the traditional resource-consuming underwriting process, allowing it to offer instantaneous quotes from multiple carrier partners.

Are you focused on Customer Service? On guiding clients through an extraordinary InsurTech platform? You may be the right person for our Customer Service Representative opening. You will assist our customers with technical problems when using our products and services. You will be responsible for resolving customer queries, recommending solutions and guiding product users through features and functionalities. To be successful in this role, you should be an excellent communicator who’s able to earn our clients’ trust. You should also be familiar with help desk software. Ultimately, you will help establish our reputation as a company that offers excellent customer support during all sales and after-sales procedures.


  • Respond to customer queries in a timely and accurate way, via phone, email or chat
  • Identify customer needs and help customers use specific features
  • Analyze and report product malfunctions (for example, by testing different scenarios or impersonating users)
  • Update our internal databases with information about technical issues and useful discussions with customers
  • Inform customers about new features and functionalities
  • Gather customer feedback and share with our Product, Sales and Marketing teams


  • The ideal candidate loves talking to people and proactively solving issues. You will be responsible for converting customers into passionate evangelists.
  • Experience as a Customer Service Representative or similar CS role for no less than 6 months.
  • Familiarity with our industry is a plus
  • Experience using help desk software and remote support tools
  • Experience with Hubspot is a plus.
  • Excellent communication and problem-solving skills
  • Multi-tasking abilities
  • Patience when handling tough cases


  • Competitive Pay
  • Matching 401k Plan
  • Unlimited Vacation Policy
  • Generous Parental Leave Program
  • Employer Paid Life Insurance and AD&D
  • Medical/Dental/Vision
  • Short/Long Term Disability
  • Employee Assistance Program

Cover Whale works to maintain the best possible environment for our employees, where individuals can learn and grow with the company. We strive to provide a collaborative environment where each person feels encouraged to contribute to their processes, decisions, planning, and culture.

We are an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, or any other characteristic protected by law.