Job Details

  • Full Time
  • Chicago, IL
  • Posted:

Head of Insurance

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 the insurtech space, and we’re currently looking to add more extraordinary people to our team. Want to know more about our culture?


What is the role?
We are seeking a Head of Insurance to join our Senior Executive Team (C-Level or SVP Level) and manage Clearcover’s core insurance functions, including underwriting, insurance product strategy, pricing, reinsurance, and risk management. This person will report directly to the CEO and be accountable for all insurance-related functions in the company.

Clearcover has grown substantially in the past 12 months and continues to build momentum. As a result, we are looking for someone who can be accountable for a large, multi-state P&L and the full-stack (licensed) insurance organization behind it. You must also be willing to look at how to grow our P&L with a first-principles lens. This role will work cross-functionally with other key stakeholders to drive the company’s growth and profit results.


What will you do? 

  • Guide insurance product strategy and roadmap with knowledge of the insurance industry, regulatory hurdles, and insurance operational challenges.
  • Ensure the achievement of continued profitability, growth and operational efficiencies of the business through assessment of risk tolerance, market appetite, and emerging risk/underwriting issues.
  • Own the roadmap, vision, and execution of our insurance product development (new features, lines of business, etc.).
  • Share overall P&L responsibility; develop insurance business/product strategies to maximize value creation through sustainable growth and high-quality customer experiences.
  • Analyze and monitor insurance product performance to make data-based decisions regarding underwriting, coverage, and pricing to drive continuous improvement.
  • Work with our Senior Leadership Team to ensure all state and product initiatives are compliant with regulations and meet with company strategies.
  • Act as a product line expert and maintain a thorough knowledge of product features and benefits, as well as industry product trends; provide product expertise to various internal areas, including technical product, engineering, growth, and claims.
  • Help us build an insurance organization that is willing to think about operations and output from first principles.


What do you need?

  • 10-15 years progressively more responsible work experience in the insurance industry. P&C leadership experience required; personal lines experience strongly preferred.
  • Direct experience applying lifetime value concepts to pricing and profitability decisions
  • Willingness to think about an organization’s economic objectives from first principles… the map is not the territory
  • Able to work hand-in-hand with our technology team to seamlessly blend insurance and product/technology goals and outcomes, as proven by successful past collaboration
  • Superior analytical, quantitative and problem-solving skills with a deep intellectual curiosity and an ability to make data-based decisions
  • Must be able to lead through influence, rather than authority only. Also must be a team player and able to operate as a “player-coach”
  • Exceptional communication skills, including the ability to develop and present clear and concise analysis and recommendations to senior management
  • Self-directed with the ability to manage and motivate others
  • Strong business acumen with a proven track record of making sound judgments backed by strong analytical skills
  • Strongly prefer a candidate that is located or willing to relocate to Chicago.


What’s in it for you?

  • Competitive compensation and benefits package
  • The ability to invest in your future and ours via a competitive equity package (i.e. massive upside potential)
  • The ability to build and shape the entire insurance organization of a rapidly growing, disruptive technology startup.
  • Reporting directly to the CEO, you will have a strong influence on Clearcover’s overall strategy and operations.


How to apply

Apply here: