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. As Staff Attorney, you’ll report directly to the VP of Legal & Compliance and serve as a key legal resource across the organization. Your primary focus will be commercial contract review and negotiation on behalf of all business partners at Pie, managed through our contract lifecycle management platform, LinkSquares. You’ll own the full contracting workflow — from intake through execution — while building strong relationships with internal stakeholders who rely on your guidance to move work forward. You’ll also lead Pie’s legal collections function, supporting...

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. As an Inside Sales Rep, you’ll serve our direct customer channel by working with small business owners and giving them the support they need. The sales team is flexible and adaptable — we navigate challenges and problem-solve quickly in service of our mission. Pie is a highly collaborative team that communicates constantly. You’ll work across teams and with stakeholders, so strong communication and coordination skills are essential. You’ll be in regular contact with customers by phone and email to sell and build relationships. How You’ll Do It Build relationships...

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. As a Senior Manager, Operations, you will play a central role in building a scalable, high-performing operations organization. Reporting to the Director of Customer Service & Operations, you will own the performance of our vendor partnerships and customer service operational model — driving accountability, efficiency, and continuous improvement across the function.  This role is well-suited for an operator who sees a landscape of manual processes not as a limitation, but as a clear roadmap for impact. You will design and implement scalable systems and workflows —...

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. As the Team Lead, Billing & Collections, you own the end-to-end process for past-due receivable collections — installment payments, short-rated policies, claim deductibles, audit surcharge fees, and additional premium from mid-term endorsements or end-of-policy audits. You are accountable for Pie's overall bad debt recovery rate and for driving collection, litigation, and settlement outcomes against internal targets. You lead a team of individual contributors alongside BPO and offshore partners, set the strategy for how every dollar of exposure gets pursued, and...

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 Medical Only Claims Adjuster will play a vital role in delivering quality claim file management and an industry-leading customer claims experience. This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers.  How You’ll Do It Claims Technical Management: Independently handle all aspects of the...

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 Payroll Partner Service Advocate is a key role for Pie's Payroll Partner team. This is a mid-level customer service team member who focuses on routine to advanced customer issues and resolves concerns and requests from payroll partners and insureds. How You’ll Do It Provide responsive, timely, and relevant service to payroll partners:   Handles email, and platform-based communication with payroll partners and cross-functional stakeholders to provide excellent customer service, Maintains SLA’s set by Payroll Partner Ops team in a consistent and efficient...

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 Manager, Premium Audit is responsible for driving measurable performance improvements across Pie's contact center and operations ecosystem. This individual contributor role owns the design, implementation, and continuous optimization of workforce management practices, technology platforms, and analytics infrastructure that enable our operations teams to deliver exceptional customer and agent experiences at scale. The role serves as a critical bridge between people, process, and technology — translating data into actionable insight and insight into operational...

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. At Pie, our “employees” are team members, and we call ourselves Pie-oneers. The Principal People Partner ensures the successful contribution of our Pie-oneers by driving people and organizational strategies that enable and empower our leaders to lead their teams to achieve their highest-impact goals and drive success across the business.   As Pie’s People team evolves, we are seeking a highly strategic yet execution-focused Principal People Partners to serve as a trusted advisor to senior leaders, driving people and organizational strategies that enable our leaders and...

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. This is a hands-on engineering role — you'll be writing production Python and SQL, building Airflow DAGs, and contributing to our Data Vault 2.0 warehouse alongside a team of staff engineers. You'll work on the data infrastructure that powers how Pie quotes, underwrites, and services small business insurance customers. The pipelines and models you build feed everything from pricing to financial reporting, which means correctness and reliability matter. You'll be expected to develop deep domain expertise in insurance and the Pie business over time. Engineers who...

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 Complex Claims Adjuster will play a critical role in delivering quality claim file management and  an industry-leading customer claims experience, by providing hands-on adjudication of catastrophic and large loss claims. This will be completed  by adhering to Pie’s Claims Best Practices, complying with regulatory and statutory requirements, and applying advanced knowledge and experience with complex negotiation strategies, structured settlements, Medicare Set-Aside requirements, and overall risk evaluation and mitigation.  This role will work with internal and...

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. As the Team Lead, Collections, you own the end-to-end process for past-due receivable collections — installment payments, short-rated policies, claim deductibles, audit surcharge fees, and additional premium from mid-term endorsements or end-of-policy audits. You are accountable for Pie's overall bad debt recovery rate and for driving collection, litigation, and settlement outcomes against internal targets. You lead a team of individual contributors alongside BPO and offshore partners, set the strategy for how every dollar of exposure gets pursued, and continuously find...

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. In this Individual contributor role, the Senior Operational Excellence Manager drives cross-functional operational improvement initiatives across multiple business domains. They design and implement programs that increase efficiency at scale, bridging operational execution with strategic enterprise thinking, and building stakeholder relationships to influence organizational change. The Senior Operational  Excellence Manager will use proven methodologies to identify multi-domain improvement opportunities and deliver measurable business value. As a member of the Operational...

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. Our Underwriters are on the front lines, interacting with our customers all day, every day. Every underwriting call, email and message has a profound impact on our business and our reputation. The average day in the life of a Pie Underwriter involves a high volume of daily transactions ranging from making underwriting decisions to issuing a certificate of insurance. We expect your role will evolve quickly as Pie grows.  How You’ll Do It Leverage workers’ compensation or commercial insurance underwriting expertise to assess medium to complex risks in order to...

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. This role serves as the connector for customer success with responsibilities to onboard/offboard agencies, ensuring they are using the self-service tools for easier support, and  coordinating our systems to match when our customers change.  In addition this  team will assist with backoffice tasks as needed that can include agency document requests and troubleshooting questions regarding agency commissions. How You’ll Do It Resolve customer emails requests (cases) with accuracy and timeliness: Provide specific assistance related to agency commission questions...

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 Senior Claims Adjuster will play a critical role in delivering quality claim file management and  an industry-leading customer claims experience., This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers..  How You’ll Do It Claims Technical Management: Independently handle all aspects of the...

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. As the Vice President of Claims Adjudication, reporting to the Chief Claims Officer, your purpose will be to collaborate in the design and execution of Pie's claims strategy and programs. In this role, you will lead Pie's claims adjudication function, ensuring the delivery of optimal claim outcomes and exceptional customer experiences. You are responsible for strategically building and leading a claims adjudication organization that executes on the overall claims strategies. You will be fostering relationships at every level both internally with team members and other...

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 Claims Adjuster will play a vital role in delivering quality claim file management and an industry-leading customer claims experience. This will be completed by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers.  How You’ll Do It Claims Technical Management: Independently handle all aspects of the workers’...

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 Senior Claims Adjuster will play a critical role in delivering quality claim file management and  an industry-leading customer claims experience., This will be completed  by adhering to Pie’s Claims Best Practices and complying with regulatory and statutory requirements. This role will work with internal and external partners to deliver best in class performance, identify and pursue claim mitigation opportunities and deliver favorable claim outcomes for Pie’s customers. How You’ll Do It Claims Technical Management: Independently handle all aspects of the...

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...

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 Director, Actuary is responsible for leading Corporate Actuarial functions for workers' compensation and other P&C lines of business. This leadership position will manage a growing team of actuaries responsible for actuarial analyses in the areas of reserving, reinsurance, pricing, ratemaking, analytics, and systems integration in support of Pie's pricing and financial goals. Duties also include enhancing enterprise risk management capabilities, applying predictive models, researching workers' compensation industry trends, and developing and delivering...