Vice President, Field Underwriting

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,

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

Skills Required
Bachelor's degree
15+ years of workers' compensation underwriting experience with accountability for portfolio results
10+ years leading underwriting organizations, including building or rebuilding teams
Track record of operating model design and change leadership
Familiarity with blended onshore/offshore underwriting models or centralized underwriting at scale
Experience recruiting, developing, and managing leaders for New Business and Renewal
Analytical fluency: ability to read loss data, model outputs, and connect data to strategy
Strong executive presence to represent function to SLT, reinsurers, and external partners
Experience in technology-forward environments (InsureTech, innovative carrier, or MGA)
CPCU, ARe, or equivalent credentials (advanced credentials preferred)
Must live and work in the United States and have access to reliable, high-speed internet