Vice President, Field Underwriting

Pie Insurance

. Own loss ratio outcomes across New Business and Renewal .

Posted 11/3/2026full-timeRemote • United StatesLead💰 $205,000 - $295,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in workers' compensation underwriting, including strategic direction for onshore/offshore models and AI-enabled workflows. Proven ability to lead and develop underwriting teams while driving performance management and operational excellence.

Highest-signal resume keywords

Workers' Compensation Underwriting ExperienceLeadership in Underwriting OrganizationsOperating Model DesignAnalytical Fluency with Loss DataCPCU or Equivalent Certification

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Underwriting StrategyRisk Selection PhilosophyPortfolio Monitoring FrameworksPerformance Management PracticesAI-Assisted WorkflowsAutomation RoadmapOnshore/Offshore Model DesignChange LeadershipData AnalysisAccountability for Portfolio Results

Soft Skills

Executive PresenceTeam DevelopmentCollaboration with External PartnersCommunication SkillsStrategic Thinking

Tools & Technologies

AI-Enabled Underwriting ToolsAutomation ToolsInsureTech PlatformsData Science Collaboration

Certifications & Qualifications

CPCUAReAdvanced Credentials

Industry Keywords

Workers' CompensationUnderwriting Best PracticesPortfolio ManagementReinsurance EngagementInnovative Carrier

About the role

Key responsibilities & impact

Own loss ratio outcomes across New Business and Renewal
Drive underwriting strategy, including appetite, authority standards, and risk selection philosophy
Partner with Corporate Underwriting on appetite, eligibility, underwriting best practices, and automation
Establish portfolio monitoring frameworks and lead underwriting review and corrective action cadence
Own the design and ongoing performance of Pie's blended onshore/offshore underwriting model
Set strategic direction for the offshore underwriting partnership
Define work segmentation among onshore, offshore, and automated channels
Coordinate human underwriting judgment with AI-assisted tools
Build and lead the Field Underwriting organization
Recruit and develop New Business and Renewal leaders
Create an internal development culture for underwriting capability
Establish the intellectual framework for workers' compensation risk selection
Drive consistent performance management practices with the People team
Shape enterprise priorities as an executive team member
Represent Field Underwriting 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 on underwriting and portfolio topics
Build Pie's external presence in the workers' compensation underwriting community
Define the strategic vision and transition roadmap for AI-enabled underwriting
Partner with Corporate Underwriting and Data Science on the automation roadmap
Lead adoption of new underwriting tools and AI-assisted workflows
Support documentation and systematization of underwriting standards

Requirements

What you’ll need

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
Track record of operating model design and change leadership
Experience with technology-forward environments such as InsureTech, innovative carrier, or MGA context preferred
Familiarity with blended onshore/offshore models or centralized underwriting at scale
Strong executive presence to represent the function to SLT, reinsurers, and external partners
Analytical fluency with loss data, model outputs, and portfolio trends
CPCU, ARe, or equivalent; advanced credentials preferred
Must live and work in the United States, excluding territories
Access to reliable, high-speed internet

Benefits

Comp & perks

Competitive cash compensation
Comprehensive health plans
Generous PTO
Future focused 401k match
Generous parental and caregiver leave
Discretionary bonuses may be granted annually to eligible team members
Core values tangibly reflected in the work