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 leading startups in the insurtech space, and we’re currently looking to add more extraordinary people to our team.

What is the role?

We are seeking a Chief Financial Officer to join our Senior Executive Team and manage Clearcover’s core financial functions, including strategic financial planning and analysis, accounting and controls, capital markets and fundraising activities, and audit and risk management. This person will report directly to the CEO and be accountable for all finance-related functions in the company.  

Clearcover is building an industry-leading, long-term focused insurance business. As a result, we are looking for someone with significant experience leading sustainable, growing insurance companies. This person will help develop strategies to balance organic and inorganic growth with the profitability goals of the business, drive key financial and capital markets activities, and be a thought-partner to other members of the Senior Executive Team. They will also work closely with the existing financial leadership team to manage the core financial operations of the company.

What will you do? 

  • Support the Board and senior executive team by proposing and evaluating key business decisions from a finance perspective, leveraging financial data, strategic insight, and rigorous analytical thinking.
  • Lead strategic capital markets activities including equity and debt fund raises, reinsurance partnerships, and relationships with current and potential investors and other strategic partners.  
  • Own the long-term financial planning process and recommend key business strategies that drive value, including through capital management, reinsurance and strategic investments
  • Oversee the departmental budgeting process and drive accountability through collaboration with senior department leaders
  • Lead the Treasury and Investment strategies and operations for the holding company and all regulated entities
  • Oversee monthly and quarterly close processes and timely financial results communication to the CEO, Board, investors and other stakeholders.
  • Ensure proper execution of all corporate accounting functions, including annual financial audits and issuance of financial statements compliant with GAAP and Statutory Accounting Principles.
  • Direct and manage a multi-disciplined finance team for both the holding company and all regulated entities
  • This role reports directly to the CEO and offers the chance to play a key role in scaling a high-potential company.

What do you need?

  • 15 years of progressive work experience in the insurance industry.
  • Capital markets experience in equity, debt and reinsurance markets.
  • Familiarity with recurring-revenue businesses and developing and managing cohort-based financial metrics.
  • 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 and insurance teams as a strategic thought partner, as proven by successful past collaboration with senior stakeholders.
  • 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. 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 and our Board of Directors.
  • Self-directed with the ability to manage and motivate others.

What's in it for you? 

  • Reporting directly to the CEO, you will have a strong influence on Clearcover’s overall strategy and operations
  • An established, high-performing finance organization with key leadership in place and critical ties to our product and insurance teams  

But wait, there’s more:

As a people-first company, your health and well-being is a priority at Clearcover. We offer comprehensive benefits for individuals and families:

  • Medical. We offer rich and affordable BCBS plans for you and your dependents. If you select the high deductible health plan, we offer an HRA and contribute to your HSA.
  • Dental and vision. We cover 100% of dental and vision premiums for you and your dependents.
  • Pre-tax benefits, disability, and life insurance. 
  • 401(k). We contribute 3%, even if you contribute nothing.

We’ve also curated a stack of perks and benefits that stretch beyond the expected. Our people have access to:

  • Generous vacation, 12 paid holidays, and parental leave.
  • Equity in the company (plus an evergreen plan) and an annual bonus program.
  • Employee resource groups and mental health workshops.
  • Top of the line hardware and meeting free “Focus Fridays”. 

We’re a remote first company, having paved the way for flexible work locations and continue to offer this flexibility. If you are local or in town visiting, you also have the choice to work from our Chicago HQ office.

To top it all off, if Clearcover is available in your state, you could have access to an employee discount on auto-insurance! Excited to learn more? Complete the application below!

Clearcover is an Equal Opportunity Employer (EOE) that welcomes and encourages all applicants to apply regardless of age, race, color, religion, sex, sexual orientation, gender identify and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law.

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