VP- Senior Counsel

| 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.

Job Summary

Develop, grow and lead Clearcover’s Corporate Legal Department by overseeing insurance regulatory and compliance functions, vendor and strategic alliance negotiations and legal administration along with providing consultation to the Company’s leadership. This role will also supervise claim investigations and serve as the Corporate Secretary for all holding companies and insurance subsidiaries.

 Job Responsibilities

  • Execute corporate legal strategy by organizing the best mix of internal and external legal services through the balance of benefit and cost while mitigating legal and regulatory exposures relative to the Company’s operations 
  • Lead insurance regulatory and compliance functions by adhering to standards defined at the state and federal level to include ensuring good relations with states’ insurance departments
  • Provide corporate legal and regulatory advice to the Company’s executive management, the holding company and subsidiary Board of Directors, Executive Management team and Board and Executive committees
  • Drive a partnership that both enhances Business Unit Support team capabilities and embeds legal professionals into the go-to-market strategy and decisions that will drive Company performance
  • Manage all claims litigation, bad faith litigation, arbitration along with state and federal relations involving insurance regulators. Select and manage external claims counsel as needed
  • Manage policy creation and other contract language to ensure contracts are up-to-date and adhere to the applicable state and federal regulator statues
  • Provide input and lead aspects of the Comany’s ERM and internal controls framework
  • Advise Human Resources to provide legal advice around benefits, employee relations, and other sensitive issues and evaluate potential employment practice risks 

Experience and Education Requirements

  • Juris Doctor degree, membership of Illinois Bar preferred
  • Previous experience as a Corporate Counsel or Assistant General Counsel at an insurance company
  • Experience in building strong governance and internal control procedures
  • Experience in building a Legal function, particularly in a rapid growth environment
  • Track record of working closely with and being seen as a trusted partner by colleagues across all parts of the business
  • Excellent collaborative and problem-solving skills
  • Understanding of operating in the highly regulated industry of insurance with strong relationships with the State Departments of Insurance across the United States
  • Experience in the legal functions related to auto claims with a focus on claims litigation

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

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
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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