Head of Accounting

| Chicago

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’s you’ll do? 
We are looking for a Controller to help build a world class accounting function.  The Corporate Controller will report to the VP of Finance and primarily be responsible for leading the accounting and financial reporting for the organization to ensure the Company remains in compliance with all regulatory and statutory requirements. In addition, the Corporate Controller will provide accurate and timely information to the business to ensure the company achieves its strategic objectives. We're looking for an individual who is a self-starter, is comfortable leading a team, and has the experience, ability and drive to seek out areas which need refinement and improvement.

We promise this is the most fun you’ll have in your career and also the hardest thing you’ll do.  Still interested? Here’s what you need to know:

What are your responsibilities?

  • Enhance the existing monthly, quarterly and annual close process

  • Statutory reporting as well as all regulatory reporting to the NAIC and DOIs

  • Ownership of all monthly, quarterly and annual financial statements

  • Identify, implement and oversee the execution of necessary financial processes, policies, procedures and controls to ensure compliance with US GAAP and all applicable tax laws

  • Organize and drive all closing and consolidation processes, including monthly account reconciliations, to track and safeguard company assets and to ensure that all financial statements and reporting are timely, accurate, and according to US GAAP

  • Serve as the primary interface with external audit firm in the Company's annual financial audit

  • Serve as the primary interface with the DOI for the insurance company entity

  • Other duties as assigned (we are a small team and thus we all roll up our sleeves to get things done across all finance functions)

Where is this role located?

  • The headquarters is in downtown Chicago, IL.  Madison, WI area is also an option

What do you need?  

  • 5+ Years experience in finance and accounting with in depth knowledge and experience in statutory reporting

  • Analytical and problem solving skills with the ability to learn and apply technologies to address business challenges. Knowledge of process improvement or process re-engineering concepts a plus.

  • Financial reporting, business reporting and analysis, and/or experience with business intelligence technologies, databases or data management platforms as well as accounting and finance business applications

  • Positive attitude

What's in it for you?

  • Unlimited vacation, we hire adults 
  • Equity for all employees, so you own a piece of the pie too 
  • Dental and Vision, we've got you covered 100%
  • Medical, we cover 90% of your premium, 75% of your dependents and contribute to your HSA and HRA (cha-ching)
  • We invest in your future by contributing 3% of your salary to a 401(K), even if you don't
  • Come to work pre-taxed through our FSA commuter benefits 
  • and yes, we have unlimited LaCroix, beer, snacks and the occasional ice cream social 
Read Full Job Description


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
Open office floor plan
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
Onsite Gym
Retirement & Stock Options Benefits
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
Company sponsored family events
Acme co. sponsors family oriented events Semi-annually.
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
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