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.

About the role

• 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. 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. 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. 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.

Qualifications

• Bachelor's degree; advanced degree a plus.
• 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.
• 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.

Skills

• Strategic thinking and execution.
• Leadership and team management.
• Underwriting expertise.
• Technology and innovation.
• Communication and collaboration.

Benefits

• Competitive cash compensation
• Comprehensive health plans
• Generous PTO
• Future-focused 401k match
• Generous parental and caregiver leave

Pay

$205,000—$295,000 USD

Schedule

Remote