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.
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.
- 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
- 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 InformationUnless 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 InformationPie 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.
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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
Skills Required
- High school diploma or GED
- Bachelor's degree or some college coursework
- Minimum 3 years of underwriting experience
- Experience underwriting workers' compensation or commercial insurance risks
- Intermediate to advanced knowledge of workers' compensation class codes
- Ability to evaluate risk and sell product in direct-to-business market
- Ability to execute processes while handling a high volume of transactions
- Experience verifying businesses using resources like Google, Yelp, LinkedIn, Facebook
- Experience with Insurity, HubSpot, and Salesforce
- Experience underwriting for payroll partners
- Strong expertise in the California workers' compensation market
- Must live and work in the United States (territories excluded)
- Access to reliable, high-speed internet
What the Team is Saying
Pie Insurance Compensation & Benefits Highlights
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Healthcare Strength — Employee medical, dental, and vision premiums are covered in full for individuals, complemented by HSA contributions and options like Health and Dependent Care FSAs that reduce out-of-pocket costs.
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Parental & Family Support — Paid parental leave for the first three months, a defined return-to-work plan, and separate caregiver leave indicate meaningful support for growing families and caregivers.
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Retirement Support — A 401(k) with employer contributions is offered, and overall total rewards are enhanced by long-term elements such as retirement support alongside ownership opportunities.
Pie Insurance Insights
What We Do
Pie is transforming small business insurance. Our team of seasoned technology and insurance experts are on a mission to empower small businesses to thrive by making insurance affordable and as easy as pie.
Why Work With Us
Our team of seasoned technology and insurance experts is on a mission to make insurance less expensive, simpler, and more transparent for small business owners. In the process, we’re creating a workplace where people thrive and ideas become actions.
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Pie Insurance Teams
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Remote Workspace
Employees work remotely.
As a fully remote company, Pie supports our Pie-oneers in working in a U.S. location that’s best for them.
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