Underwriter, Workers' Compensation

pieinsurance

United States

Posted Jun 17, 2026

Other
Remote
Underwriting Field

Job description

Pie's mission is to empower small businesses to thrive by making commercial insurance affordable and as easy as pie. We leverage technology to transform how small businesses buy and experience commercial insurance.

Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.

Our Underwriters are on the front lines, interacting with our customers all day, every day. Every underwriting call, email and message has a profound impact on our business and our reputation. The average day in the life of a Pie Underwriter involves a high volume of daily transactions ranging from making underwriting decisions to issuing a certificate of insurance. We expect your role will evolve quickly as Pie grows.

How You’ll Do It

Leverage workers’ compensation or commercial insurance underwriting expertise to assess medium to complex risks in order to underwrite and bind new and renewal coverage.
Quickly and effectively decide each request through the use of Pie’s underwriting guidelines and known risk exposures and loss frequency and severity.
Achieve profitable growth through appropriate risk evaluation while building and maintaining outstanding payroll partner customer relationships.
Prioritize and resolve payroll partner customer inquiries for documentation or support.
Provides technical assistance to the payroll partner sales team and customers regarding policy and endorsement provisions and underwriting acceptability for designated insurance coverages.
Maintain strong industry knowledge on commercial insurance underwriting expertise and changes in market/account positions. Develop and maintain full knowledge of all forms, coverages, ratings, and manuals for the specific line being underwritten.
Participate in review and evaluation of risk portfolio, making recommendations on book management issues.
Take on other tasks, responsibilities and projects as needed.

Travel Requirements

Some travel could be required in this position, up to 10% travel.

The Right Stuff

Educational Background:

High School diploma or GED required. Bachelor's degree or equivalent experience with some college coursework is preferred

Experience:

Minimum 3 years of underwriting experience or equivalent is required
Intermediate to advanced knowledge of workers’ compensation class codes
Ability to sell our product while simultaneously discerning risk characteristics within the direct to business market.
Ability to balance the outstanding execution of processes while handling a high volume of transactions
Experience with Insurity, HubSpot and Salesforce preferred
Verifying businesses using various resources and databases like Google, Yelp, LinkedIn, Facebook and similar sites
Experience underwriting insurance for payroll partners is very valuable.
Strong expertise in the California workers' compensation market is preferred

The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.

Base Compensation Range

$80,000—$100,000 USD

Compensation & Benefits

Competitive cash compensation
Comprehensive health plans
Generous PTO
Future focused 401k match
Generous parental and caregiver leave
Our core values are more than just a poster on the wall; they’re tangibly reflected in our work

Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.

Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.

Location Information

Unless otherwise specified, this role is remote. Remote team members must live and work in the United States (territories excluded) and have access to reliable, high-speed internet.

Additional Information

Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.

Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.

Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy.

Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.

Pie Named to 2025 America's Best Startup Employers

Pie Insurance 2025 State of Workplace Safety Report

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