Vice President, Field Underwriting

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.

The VP, Field Underwriting owns Pie's underwriting P&L and the execution engine behind it. Reporting to the Chief Underwriting Officer and operating as a member of the executive team and peer to the VP of Insurance Product and Pricing, this leader is accountable for portfolio results, team performance, and the operating model that delivers them. The VP shapes company priorities alongside functional accountability — that means making enterprise-first calls when function and enterprise are in tension. They define how Field UW operates for the next several years: who it hires, how the onshore/offshore model evolves, what the AI-enabled underwriting function looks like at scale, and what underwriting excellence means for Pie's customers. This role partners closely with Corporate Underwriting on the automation roadmap, providing the field execution perspective that drives what gets built next. Someone who has managed a steady-state function will not thrive here. Someone who has built and restructured will.

How You'll Do It

Own Underwriting Results and Portfolio Performance

• Own loss ratio outcomes across New Business and Renewal.
• Drive underwriting strategy in partnership with the VP of Insurance Product and Pricing and the CUO, including appetite, authority standards, and risk selection philosophy.
• Partner with Corporate Underwriting on appetite, eligibility, and underwriting best practices development; anchor those decisions in field execution experience and portfolio loss data.
• Establish portfolio monitoring frameworks that surface emerging trends before they compound into loss problems.
• Help lead the underwriting review and corrective action cadence across the function.

Design and Operate the Blended Underwriting Model

• Own the design and ongoing performance of Pie's blended onshore/offshore underwriting model.
• Set strategic direction for the offshore underwriting partnership, including quality standards, performance accountability, and scope of work over time.
• Define how work is segmented among onshore, offshore, and automated channels as the business scales.
• Build toward Pie's AI roadmap: own the coordination of human underwriting judgment and AI-assisted tools as those capabilities mature.

Build and Lead the Organization

• Build and lead the Field Underwriting organization.
• Recruit and develop leaders for New Business and Renewal.
• Create a development culture that grows underwriting capability from within rather than relying entirely on external hiring.
• Establish and maintain the intellectual framework for WC risk selection across the function, partnering with Corporate Underwriting to ensure field execution reflects sound, consistent underwriting judgment.
• Drive consistent performance management practices across the team, partnering with the People team throughout the full team member lifecycle.

Lead Strategically and Represent the Function Externally

• Actively shape enterprise priorities as a member of the executive team; represent Field UW's perspective while defaulting to what is best for Pie when function and enterprise priorities are in tension.
• Represent the Field UW function in SLT discussions on growth strategy, capital allocation, and competitive positioning.
• Partner with Business Development and Agency Management on key account strategy and agent-facing priorities.
• Engage with reinsurers, strategic partners, and regulators as needed on underwriting and portfolio topics.
• Build Pie's external presence in the workers' compensation underwriting community; contribute to industry dialogue in ways that strengthen Pie's positioning as an underwriting-led InsureTech.

Technology and Operating Model

• Own the strategic vision for AI-enabled underwriting at Field UW: define what the function looks like when AI handles the repeatable work, where human judgment is irreplaceable, and what the transition roadmap is. Corporate Underwriting builds it; the VP defines the destination.
• Partner with Corporate Underwriting and Data Science on the automation roadmap: surface where human judgment is being applied unnecessarily and validate where automation is ready to take work off the team.
• Lead field-level adoption of new underwriting tools and AI-assisted workflows as Pie's capabilities grow; ensure the team is building capability, not dependency.
• Integral in the development of the documentation and systematization of underwriting standards — the inputs Corporate Underwriting needs to build and refine the rules and models that drive automation.

The Right Stuff

Educational Background:

• Bachelor's degree; advanced degree a plus.

Experience: 

• 15+ years of workers' compensation underwriting experience with demonstrated accountability for portfolio results.
• 10+ years leading underwriting organizations, including experience building or rebuilding a team, not just running one.
• Track record of operating model design and change leadership, not just execution management.
• Experience with technology-forward environments: InsureTech, innovative carrier, or MGA context preferred.
• Familiarity with blended onshore/offshore models or centralized underwriting at scale.
• Strong executive presence: capable of representing the function to SLT, reinsurers, and external partners.
• Analytically fluent: reads loss data, model outputs, and portfolio trends with confidence; able to connect data to strategy.
• CPCU, ARe, or equivalent; advanced credentials 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$205,000—$295,000 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.

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