Who's Clearcover?

Clearcover is the smarter car insurance company. We use powerful technology to offer everyday drivers better coverage for less money. We’re proud to be one of the fastest growing startups in Chicago, and we’re currently looking to add a few more extraordinary people to our team. 

What is an Underwriting Specialist?

Clearcover Underwriting Specialists assess and resolve all questions or issues related to whether policies meet our underwriting guidelines. They are the Subject Matter Experts that Customer Experience (CX) team members contact when there is ambiguity or possible risk around a policy. USs leverage a combination of investigative skills, insurance knowledge, and customer service to assess risk and determine appropriate underwriting outcomes. For this role, we're looking for someone who has Underwriting or Agent experience and looking to move to a fast-paced, exciting startup culture. They should be fluent in policy contract jargon and well versed in industry leveraged resources such as APCIA and other compliance tools when needed. 

What will you do?

  • Maintain and iterate on underwriting processes to simplify tasks for the CX department
  • Use your keen investigative skills to identify the need for and then obtain additional information from policyholders when necessary
  • Analyze all pertinent data to identify and assess acceptability of risks according to established Underwriting guidelines and manuals
  • Create Letters of Experience 
  • Manage Cancellation and Renewal activities including creating pertinent notices for customers
  • Investigate and act upon financial chargebacks 
  • Keep up-to-date on state/territory issues and regulations, industry activity and trends, and proactively work with other business units to leverage this information in order to ensure appropriate risk management
  • Provide proactive feedback on the underwriting guidelines and processes within our different territories to help drive positive unit economics for different segments of business

What do you need? 

  • 3-5 years insurance industry experience, preferably in Underwriting or as an Agent
  • The ability to successfully work independently and as part of a team in a constantly-changing environment
  • Demonstrated problem solving skills
  • Effective verbal, writing, and listening skills
  • Ability to exercise sound judgment when reviewing policy concerns, make decisions, and learn from mistakes 
  • An obsessive attention to detail (you can find Waldo in the blink of an eye!)
  • Flexibility and adaptability to prioritize a fluctuating workload
  • A strong technical aptitude, with the ability to master new systems quickly and efficiently


Customer Experience
Detail Oriented