Clearcover is revolutionizing the industry, putting our customers in the driver's seat. Founded in 2016, Clearcover is built on a simple premise: provide affordable, hassle-free car insurance with one of the industry's fastest claims experiences. We challenge the status quo, redefining what it means to truly put the customer first.

We're rapidly growing and recognized for it! Clearcover has been featured on the Inc. 5000 Fastest Growing Privately Held Companies list and the Deloitte Technology Fast 500™ list, raising over $560 million in funding to date.

We've also been honored on Insurance Business America's Top Insurance Employers list and CNBC's World's Top Insurtech Companies, with Forbes naming us one of America's Best Insurance Companies in 2025.

What is an Estimating Supervisor?

The Estimating Supervisor has a unique opportunity to impact Clearcover and its customers while leading daily estimating operations.

For this role, we're looking for someone who is excited to join a fast-paced, startup culture, and brings with them experience managing staff appraisers (field and virtual) and related vendors.

What will you do as an Estimating Supervisor?

Oversees all estimating activities with established claims policy and estimating procedures
Build and reinforce performance standards, driving accountability and a culture of continuous improvement
Identify and assess internal trends by leveraging data and industry leading technology to objectively assess team performance
Direct the selection, evaluation, compensation, transfer, and termination of claims personnel, in accordance with established personnel policies and practices
Create clarity in ambiguity, continuing to refine established processes and develop new best practices
Assist in evaluating and monitoring claims estimating partner relationships
Handle customer complaints, provide appropriate solutions and alternatives, follow up to ensure resolution
Maintain knowledge base of training materials, standard procedures, and shared partner guidelines
Handle and respond to DOI, BBB, and DV claims and complaints in a timely and compliant manner.
Provide in-depth reporting on claims metrics and communicate results to executive leadership
During periods of peak volume, manage large amounts of incoming and outgoing customer interactions (calls, texts)
Drive commitment to and maintenance of outstanding performance
Work closely with cross-functional teams to drive alignment, solve complex problems, and support informed decision-making

What do you need as an Estimating Supervisor?

Bachelor's Degree, or commensurate work experience
A minimum of 7+ years experience in auto physical damage estimating with at least 3+ years in a leadership or supervisory role at an P&C carrier is required
Strong technical background with substantial experience assessing suspension, mechanical, and structural damages - both field and remote experience is a plus
Experience using Mitchell Estimating software is preferred
Ability to obtain and maintain an adjuster’s license as required
Experience handling diminished value claims is a plus and will support the team's ability to assess complex loss scenarios more holistically.
Strong knowledge of the claims Total Loss process including advanced charges and salvage best practices
Strong communication skills with the ability to set clear expectations and deliver constructive feedback in real time to address gaps and opportunities
Florida claims handling experience is a plus

Base Compensation Range:

$80,000 - $100,000 annually (USD)

Did you know that women and minorities are less likely to apply to a position if they don’t match 100% of the job qualifications? Don’t let that be the reason you miss out on this opportunity! We encourage you to apply anyway. Don’t count yourself out!

But wait, there’s more:

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

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.
Generous vacation, 12 paid holidays, and parental leave.
Equity in the company and an annual bonus program.

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. Because we are a remote first company, we ask that your internet can keep up with our pace.

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 identity and/or expression, national origin, disability, veteran status, marital or parental status, ancestry, citizenship status, pregnancy or other reasons prohibited by law. Clearcover is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at hr@clearcover.com.

Pay Range: $80,000 - $100,000 per year

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