[Hiring] Vice President, Field Underwriting @Pie Insurance

Role Description

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.

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, this leader is accountable for portfolio results, team performance, and the operating model that delivers them.

• 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.
  • Partner with Corporate Underwriting on appetite, eligibility, and underwriting best practices development.
  • Establish portfolio monitoring frameworks that surface emerging trends.
  • 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.
  • Define how work is segmented among onshore, offshore, and automated channels.
  • Build toward Pie's AI roadmap.
• 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.
  • Drive consistent performance management practices across the team.
• Lead Strategically and Represent the Function Externally
  • Actively shape enterprise priorities as a member of the executive team.
  • Represent the Field UW function in SLT discussions.
  • Partner with Business Development and Agency Management on key account strategy.
  • Engage with reinsurers, strategic partners, and regulators as needed.
  • Build Pie's external presence in the workers' compensation underwriting community.
• Technology and Operating Model
  • Own the strategic vision for AI-enabled underwriting at Field UW.
  • Partner with Corporate Underwriting and Data Science on the automation roadmap.
  • Lead field-level adoption of new underwriting tools and AI-assisted workflows.
  • Integral in the development of the documentation and systematization of underwriting standards.

Qualifications

• Bachelor's degree; advanced degree a plus.
• 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.
• Strong executive presence.
• Analytically fluent.
• CPCU, ARe, or equivalent; advanced credentials preferred.

Requirements

• To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications.
• All AI-powered outputs are still subject to human oversight and decision-making at multiple stages of the process.

Benefits

• Base Compensation Range: $205,000 — $265,000 USD
• Competitive cash compensation
• Comprehensive health plans
• Generous PTO
• Future focused 401k match
• Generous parental and caregiver leave
• Discretionary bonuses to eligible team members based on company performance.

Location Information

• This role is remote. Remote team members must live and work in the United States (territories excluded).
• Must have access to reliable, high-speed internet.

Additional Information

• Pie Insurance is an equal opportunity employer.
• Pie Insurance participates in the E-Verify program.
• Pie Insurance is committed to protecting your personal data.
• Safety First: Pie Insurance is committed to your security during the recruitment process.