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. 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 and peer to the VP of Insurance Product and Pricing, this leader is accountable for portfolio results, team performance, and the operating model that delivers them. The VP shapes company priorities alongside functional accountability — that means making enterprise-first calls when function and enterprise are in tension. They define how Field UW operates for the next several years: who it hires, how the onshore/offshore model evolves, what the AI-enabled underwriting function looks like at scale, and what underwriting excellence means for Pie's customers. This role partners closely with Corporate Underwriting on the automation roadmap, providing the field execution perspective that drives what gets built next. Someone who has managed a steady-state function will not thrive here. Someone who has built and restructured will.

Responsibilities

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; 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; 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 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; Drive consistent performance management practices across the team; Actively shape enterprise priorities as a member of the executive team; 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; 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

Requirements

Bachelor's degree; 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; 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

Nice to have

Advanced degree a plus; Experience with technology-forward environments: InsureTech, innovative carrier, or MGA context preferred; Advanced credentials preferred

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; Discretionary bonuses