Remote VP, Field Underwriting & AI-Driven Growth

Pie Insurance Group; United States; On-site; USD 205,000 - 295,000; Full time

Benefits offered by this job

Competitive cash compensation

Generous PTO

Future focused 401(k) match

Generous parental and caregiver leave

Job summary

Pie Insurance Group is seeking a VP, Field Underwriting to own underwriting P&L, portfolio performance, and the operating model at scale. You will shape the offshore/onshore balance, AI-enabled workflows, and the field execution engine in collaboration with Corporate Underwriting.

You will lead a growing Field Underwriting organization, recruiting leaders for New Business and Renewal, and ensuring rigorous performance management in a fast-paced InsureTech environment.

Qualifications

• 15+ years of workers' compensation underwriting experience.
• 10+ years leading underwriting organizations.
• Track record of operating model design and change leadership.
• Experience with technology-forward environments: InsureTech, innovative carrier, or MGA context preferred.
• Familiarity with blended onshore/offshore models or centralized underwriting at scale.
• CPCU, ARe, or equivalent; advanced credentials preferred.

Responsibilities

• Own underwriting results and portfolio performance across New Business and Renewal.
• Design and operate Pie's blended onshore/offshore underwriting model and AI roadmap.
• Build and lead the Field Underwriting organization and develop leaders for New Business and Renewal.
• Drive enterprise-aligned strategic priorities and represent Field UW in SLT discussions.
• Lead the adoption of underwriting tools and AI-assisted workflows and document standards.

Skills

Underwriting leadership

Portfolio management

Executive communication

Data-driven decisions

Education

Bachelor's degree

Advanced degree a plus

Job description

Pie Insurance Group is seeking a VP, Field Underwriting to own underwriting P&L, portfolio performance, and the operating model at scale. You will shape the offshore/onshore balance, AI-enabled workflows, and the field execution engine in collaboration with Corporate Underwriting.

You will lead a growing Field Underwriting organization, recruiting leaders for New Business and Renewal, and ensuring rigorous performance management in a fast-paced InsureTech environment.