Vice President, Field Underwriting
Pie Insurance · Remote · United States · $205k–$295k
Posted by Pie Insurance on their careers site · View the original posting
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Open 116 days
Hiring? Uncertain · Open 116 days.
The posting, as Pie Insurance wrote it
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.
Like our small business customers, we are a diverse team of builders, dreamers, and entrepreneurs who are driven by core values and operating principles that guide every decision we make.
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.
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 f
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are still subject to human oversight and decision-making at multiple stages of the process. By submitting your application, you acknowledge and consent to Pie utilizing these AI technologies to assist in our evaluation process.
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
Making every part of working with us "Easy as Pie" - including our offer process. When we find someone we'd like as a Pie-oneer (a member of our team), we move quickly to put together a fair offer based on your skills, experience, location, and compensation expectations.
Each year Pie reviews company performance and may grant discretionary bonuses to eligible team members.
Location Information
Unless otherwise specified, this role is remote. Remote team members must live and work in the United States ( territories excluded ) and have access to reliable, high-speed internet.
Additional Information
Pie Insurance is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, marital status, age, disability, national or ethnic origin, military service status, citizenship, or other protected characteristic.
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Pie Insurance is committed to protecting your personal data. Please review our Privacy Policy .
Safety First: Pie Insurance is committed to your security during the recruitment process. We will never ask you for credit card information or ask you to purchase any equipment during our interview or onboarding process.