Underwriter, Small Commercial Workers’ Compensation/Commercial Auto

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. As part of Pie’s Underwriting team you’ll be responsible for not only the day-to-day decision making, but also providing guidance and expertise for how our underwriting evolves, grows and scales as we press forward.

How You’ll Do It

• Leverage workers’ compensation or commercial Auto 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 partner customer relationships.
• Prioritize and resolve customer inquiries for documentation or support.
• Provides technical assistance to support teams and customers regarding policy and endorsement provisions and underwriting acceptability for designated insurance coverages.
• Maintain strong industry knowledge on commercial insurance underwriting concepts and changes in market/account positions. 
• Develop and maintain full knowledge of all forms, coverages, ratings, and manuals for each of the specific lines of business 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.

The Right Stuff

• High School diploma or GED required. Bachelor's Degree or equivalent experience with some college coursework is preferred.
• 3+ years of commercial underwriting experience or equivalent is required.
• Aptitude for building and maintaining strong partner relationships through excellence in service, engagement & follow through in conjunction with our Business Development and Partner Experience teams.
• Intermediate to advanced knowledge of workers’ compensation class codes, loss mitigation strategies, and other underwriting concepts.
• Intermediate to advanced knowledge of commercial auto underwriting concepts including evaluation of multiple types of risks ranging from fleets of PPTs to Small Trucking.
• 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.
• Willing to work in an iterative development environment with an ever changing landscape filled with possibilities and questions.

Travel Requirements

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

Effective 05/24/2025 - 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. All AI-reviewed applications are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to it being reviewed using these AI technologies to assist in our evaluation process.

Base Compensation Range$80,000—$100,000 USD

Compensation & Benefits 

• 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 tha