Pie Insurance Jobs Hiring Now
Pie Insurance is hiring for 19 open roles on Migrate Mate as of July 16, 2026, concentrated in business operations and business analysis, with listed salaries up to about $295,000. Migrate Mate updates Pie Insurance's live openings daily. Pie Insurance is a workers' compensation insurance company serving small businesses across the United States.
Find Pie Insurance JobsOverview
Pie Insurance hiring data on Migrate Mate, as of July 16, 2026.
- Open jobs
- 19
- Top team
- Business Operations
- Seniority
- Manager level or above
- Work type
- 89% remote or hybrid
- Top location
- Denver
- Salary range
- $65,000–$295,000
Listed salaries for Pie Insurance roles on Migrate Mate range from about $65,000 to $295,000 per year across 19 open roles, as of July 16, 2026.
Open Roles at Pie Insurance
Showing 19 of 19+ Pie Insurance jobs
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 for WC risk selection across the function, partnering with Corporate Underwriting to ensure field execution reflects sound, consistent underwriting judgment.
- Drive consistent performance management practices across the team, partnering with the People team throughout the full team member lifecycle.
Lead Strategically and Represent the Function Externally
- Actively shape enterprise priorities as a member of the executive team; represent Field UW's perspective while defaulting to what is best for Pie when function and enterprise priorities are in tension.
- 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; contribute to industry dialogue in ways that strengthen Pie's positioning as an underwriting-led InsureTech.
Technology and Operating Model
- Own the strategic vision for AI-enabled underwriting at Field UW: define what the function looks like when AI handles the repeatable work, where human judgment is irreplaceable, and what the transition roadmap is. Corporate Underwriting builds it; the VP defines the destination.
- Partner with Corporate Underwriting and Data Science on the automation roadmap: surface where human judgment is being applied unnecessarily and validate where automation is ready to take work off the team.
- Lead field-level adoption of new underwriting tools and AI-assisted workflows as Pie's capabilities grow; ensure the team is building capability, not dependency.
- Integral in the development of the documentation and systematization of underwriting standards — the inputs Corporate Underwriting needs to build and refine the rules and models that drive automation.
The Right Stuff
Educational Background:
- Bachelor's degree; advanced degree a plus.
Experience:
- 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.
- 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: 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; advanced credentials preferred.
The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs 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.
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.
Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.
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.
Pie Named to 2025 America's Best Startup Employers
Pie Insurance 2025 State of Workplace Safety Report
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 for WC risk selection across the function, partnering with Corporate Underwriting to ensure field execution reflects sound, consistent underwriting judgment.
- Drive consistent performance management practices across the team, partnering with the People team throughout the full team member lifecycle.
Lead Strategically and Represent the Function Externally
- Actively shape enterprise priorities as a member of the executive team; represent Field UW's perspective while defaulting to what is best for Pie when function and enterprise priorities are in tension.
- 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; contribute to industry dialogue in ways that strengthen Pie's positioning as an underwriting-led InsureTech.
Technology and Operating Model
- Own the strategic vision for AI-enabled underwriting at Field UW: define what the function looks like when AI handles the repeatable work, where human judgment is irreplaceable, and what the transition roadmap is. Corporate Underwriting builds it; the VP defines the destination.
- Partner with Corporate Underwriting and Data Science on the automation roadmap: surface where human judgment is being applied unnecessarily and validate where automation is ready to take work off the team.
- Lead field-level adoption of new underwriting tools and AI-assisted workflows as Pie's capabilities grow; ensure the team is building capability, not dependency.
- Integral in the development of the documentation and systematization of underwriting standards — the inputs Corporate Underwriting needs to build and refine the rules and models that drive automation.
The Right Stuff
Educational Background:
- Bachelor's degree; advanced degree a plus.
Experience:
- 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.
- 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: 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; advanced credentials preferred.
The use of AI in Application Review: To support a fair, efficient, and consistent hiring process, we use AI-powered tools to assist in the initial screening of applications. These tools help us identify qualifications and prior work experiences that align with the requirements of the role. We may also use AI assistant video tools during interviews to support note-taking and candidate evaluation. All AI-powered outputs 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.
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.
Pie Insurance participates in the E-Verify program. Please click here, here and here for more information.
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.
Pie Named to 2025 America's Best Startup Employers
Pie Insurance 2025 State of Workplace Safety Report
Job Roles at Pie Insurance
Working at Pie Insurance
Pie Insurance's 19 open roles are manager level or above, and about 89% are remote or hybrid. The most active teams are business operations, business analysis, and program management. Pie Insurance is a workers' compensation insurance company that provides coverage to small businesses. Its open roles span claims, underwriting, actuarial, premium audit, data engineering, finance, and people operations functions. Most Pie Insurance roles are based in Denver and Remote.
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Browse jobs by rolePie Insurance Jobs: Frequently Asked Questions
How many jobs is Pie Insurance hiring for right now?
Pie Insurance is hiring for 19 open roles on Migrate Mate as of July 16, 2026, updated daily, concentrated in business operations and business analysis. Roles span claims, underwriting, actuarial, premium audit, finance, and people operations. Migrate Mate pulls Pie Insurance's listings continuously so the count reflects what is actively open.
What kinds of roles does Pie Insurance hire for?
The most active teams are business operations, business analysis, and program management. Pie Insurance hires across workers' compensation claims, underwriting, premium audit, actuarial, data engineering, accounting, internal controls, and people operations. Positions range from individual contributors to senior analysts, managers, and director-level leaders, and most postings are manager level or above.
Are Pie Insurance jobs remote or in-person?
Mostly remote. About 89% of Pie Insurance's open roles on Migrate Mate are remote or hybrid as of July 16, 2026, with the rest based in Denver. Each Pie Insurance listing shows its work location so you can filter before applying.
How do I apply to a job at Pie Insurance?
Find a Pie Insurance role on Migrate Mate, then follow the listing through to Pie Insurance's own careers page to submit your application. Pie Insurance manages its hiring process directly, including screening, interviews, and offers. Migrate Mate keeps Pie Insurance's listings current so you can browse what is open today.
What do Pie Insurance jobs pay?
Listed salaries for Pie Insurance roles on Migrate Mate range from about $65,000 to $295,000 per year as of July 16, 2026, with most postings at manager level or above. Exact pay is set by Pie Insurance and shown on each listing.
Does Pie Insurance hire entry-level?
Most of Pie Insurance's open roles on Migrate Mate are manager level or above as of July 16, 2026. Entry-level openings are limited. Check individual Pie Insurance listings for stated experience requirements.
Where is Pie Insurance hiring?
Most Pie Insurance roles are based in Denver and Remote, and about 89% offer remote or hybrid work as of July 16, 2026. Migrate Mate shows the location on each listing.