Underwriter, Workers' Compensation

Role 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.

Our Underwriters are on the front lines, interacting with our customers all day, every day. 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.
• Provide 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.

Qualifications

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

Requirements

• 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.

Benefits

• Base Compensation Range: $80,000 — $100,000 USD.
• Competitive cash compensation.
• A piece of the pie (in the form of equity).
• Comprehensive health plans.
• Generous PTO.
• Future focused 401k match.
• Generous parental and caregiver leave.
• 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.
• 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.