Chief Financial Officer at Clearcover

| Chicago
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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.

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 has grown substantially in the past 12 months and continues to build momentum. As a result, we are looking for someone who has operated at scale and can be a thought-partner to other members of the Senior Executive Team as the Company prepares and plans for the next stage of growth. This role will work cross-functionally with other key stakeholders to drive the company’s growth and profit results. 

What will you do? 

  • Provide strategic FP&A support to the senior executive team and evaluate key business decisions with financial data, cost-benefit analyses, and rigorous analytical thinking.
  • Lead the development of Monthly and Quarterly Business reviews at the company-level.
  • Lead strategic capital markets activities including equity and debt fund raises, and manage relationships with strategic partners.
  • Build, develop and manage a multi-disciplined finance team for both Clearcover Insurance Company and Clearcover, Inc. 
  • Develop processes for tracking and managing budgets with senior division leaders
  • Manage monthly and quarterly close processes, including preparing audited financial statements and management reports.
  • Lead annual audits and ensure compliance with GAAP and Statutory Accounting Principles.
  • Manage key accounting functions, including A/R, A/P, payroll, benefits, employee expenses, stock administration, and tax.
  • This role reports directly to the CEO and offers the chance to play a key role in scaling a high-growth startup.

What do you need?

  • 10-15 years of progressive work experience in the financial industry or in high-growth startups. Progressive experience in venture capital, private equity, or investment banking is preferred. 
  • Experience raising both debt and late-stage equity capital.
  • Familiarity with direct-to-consumer subscription 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.
  • Strong business acumen with a proven track record of making sound judgments backed by strong analytical skills.

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.
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Technology we use

  • Engineering
    • KotlinLanguages
    • PythonLanguages
    • RubyLanguages
    • ScalaLanguages
    • ReactLibraries
    • Ruby on RailsFrameworks
    • PostgreSQLDatabases
    • SnowflakeDatabases


33 W Monroe, Chicago, IL 60603

An Insider's view of Clearcover

What's something quirky about your company?

It’s surprising how much we all grow to love discussing insurance. Everyone is genuinely interested in how the industry works and sharing knowledge. I think we feel we owe it to our customers to understand how insurance works, so they don’t have to. We’ve likely all thought at one point, “Wow, I never thought I’d care about insurance this much.”


Senior Software Engineer

How do you collaborate with other teams in the company?

Whether I'm working with Product to promote a feature launch or partnering with our Customer Advocate team to communicate updates to customers, I get to collaborate across teams, leverage my skills & improve my expertise every day. Clearcover nurtures a collaborative environment and encourages thinking outside the box to deliver better experiences.


Director of Communications

What are Clearcover Perks + Benefits

Volunteer in local community
Intracompany committees
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Clearcover covers 100% of the employee's dental benefits.
Vision Benefits
Clearcover covers 100% of the employee's vision benefits.
Health Insurance Benefits
Clearcover's health insurance plan is with United Healthcare with a range of plans including PPO, HDHP and HSA. If you elect an HSA, we cover your out-of-pocket deductible as an HSA contribution.
Life Insurance
Clearcover offers voluntary life insurance.
Pet Insurance
Wellness Programs
Onsite Gym
Retirement & Stock Options Benefits
401(K) Matching
Clearcover provides employees with a 401(k) contribution of 3% of an employee's annual gross pay.
Company Equity
Child Care & Parental Leave Benefits
Generous Parental Leave
Clearcover offers parental and maternal leave with up to three months of paid time off.
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Clearcover's offers Commuter Benefits, employees can save an average of 30 percent off their commute by contributing pre-tax dollars.
Company Outings
Clearcover celebrates company wins by organizing quarterly outings to a variety of places like the Escape Room, Punchbowl Social and Bounce.
Game Room
Clearcover's game room includes a state-of-the-art ping pong table, custom Nerf gun wall and a Pop-a-Shot to let employees enjoy breaks between work.
Stocked Kitchen
Some Meals Provided
Professional Development Benefits
Job Training & Conferences
Clearcover offers a stipend to each employee to invest as they choose in their own professional development.
Lunch and learns
Cross functional training encouraged
Promote from within
Time allotted for learning
Online course subscriptions available
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