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 Product 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 Product Manager will use proven methodologies to identify multi-domain improvement opportunities and deliver measurable business value. As a member of the Operational  team,...

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. With approximately 350 team members today and scaling through people and technology for the future, Pie is seeking an exceptional Director of People Operations & Total Rewards (Dir, POps & TR) to join the People leadership team. This role will shape and elevate our human resources function at a strategic level through AI, technology, and a blend of business- and people-centered approaches. The Dir, POps & TR reports to the Chief People Officer (CPO). This Director role serves as a critical member of the People, Talent & Executive Support (PTE) leadership...

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 Quality Assurance Auditor will conduct regular audits and assessments of Pie's claims handling processes to ensure adherence to Claims Best Practices, regulatory standards, and internal guidelines. This role is responsible for reviewing claim files for compliance, identifying areas of non-compliance, and recommending corrective actions to improve claims quality. The auditor will collaborate with Claims teams, prepare detailed audit reports, and support the development of quality control policies and training programs that drive continuous improvement in...

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. Working with the Accounting Manager and supporting our Controllers, you’ll be part of building out our accounting function and owning key elements of our financial close process. You’ll apply your GAAP knowledge to day-to-day accounting operations, with a roll-up-your-sleeves approach. You’ll interface with fellow Pie-oneers, vendors, partners, and related parties while being accountable for accurate and timely completion of all assigned tasks. How You’ll Do It Drive Accounting Operations: Participate in the monthly accounting close process. Prepare journal...

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 Premium Auditor I is responsible for conducting standard premium audits for routine business structures for single and multiple entities using mail, phone, and virtual platforms. This role involves reviewing payroll records, tax returns, and financial documents to ensure accurate policy coverage and compliance with regulatory guidelines. The auditor applies classification codes using NCCI, PAAS, and state-specific requirements, thoroughly documents findings, and prepares detailed audit worksheets. How You’ll Do It Core Audit Execution Conduct standard...

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 Premium Auditor II is responsible for conducting comprehensive premium audits across diverse industries using mail, phone, and virtual platforms. This role involves reviewing payroll records, tax returns, and financial documents to ensure accurate policy coverage and compliance with regulatory guidelines. The auditor applies classification codes using NCCI, PAAS, and state-specific requirements, thoroughly documents findings, and prepares detailed audit worksheets. How You’ll Do It Core Audit Execution Conduct comprehensive premium audits via mail, phone,...

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...

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 Manager, Claims Vendor Management leads Pie's Claims Vendor Management program for assigned strategic claims vendors, with a strong focus on oversight of managed care program vendors. This role manages Claims vendor relationships including managed care services (medical bill review, pharmacy benefit management, utilization review, provider networks), legal vendors (law firms and litigation support), investigative services, support vendors (transportation, translation), and API-integrated technology vendors. The Manager executes vendor strategy in partnership with...

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. Pie Insurance’s Technology team builds and operates a suite of applications and services that allow direct consumers, partners, and agents to manage commercial insurance policies. The team collaborates closely with our business partners to design and implement new features to help the company scale with increasing demand.  We are seeking highly motivated Backend Engineers who encourage an environment where engineers are thought leaders and foster a culture of diversity and inclusion. Acting as leaders across the organization on design, architecture, and best practices,...

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 Team Lead is responsible for leading a team of Adjusters and Specialists by monitoring their workloads, providing supervisory oversight for individual claim activities, and providing technical and jurisdictional direction on claims adjudication to ensure Pie is providing optimal claim outcomes and experiences for our clients.  Additionally, this role is responsible for performance management and development of direct reports. The Team Lead will report to and work directly with the Claims Manager to achieve team and departmental goals. The Team Lead will need 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. As a Digital Account Specialist at Pie, you will take full ownership of managing and growing a partner portfolio (200:1). Your role involves driving proactive business development, autonomously addressing client needs, and meeting performance quotas. You will represent Pie with professionalism and make strategic decisions to enhance client relationships and achieve organizational goals. How You’ll Do It Maintain service communication and drive outcomes with existing partners: Build and engage with outside agency partnerships to increase engagement in the form...

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 Underwriter is a pivotal team member when it comes to supporting the department with functional and operational tasks in order to help the team achieve their target deliverables. In addition to their own production requirements, the Senior Underwriter serves as the go-to representative for the team when other departments and teams are looking for additional expertise and knowledge regarding underwriting. As a Senior level contributor, this person is able to represent the underwriting team in a variety of capacities and step in for other leaders when needed....

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. Overall, the Total Rewards Manager is responsible for the strategy and execution of that strategy for base compensation, short term incentive compensation, long term incentive compensation, equity, benefits, and wellness. The work requires partnership with People Partners and Recruiters as well as the executive team, including the Director of People Operations, SVP of People and Talent, CEO, and CFO. How You’ll Do It Serve as the Compensation Partner to deliver strategic compensation support to the organization: Provide consultation and guidance to key...

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. Reporting directly to our Manager of Quality & Training, the Quality & Training Analyst is responsible for ensuring consistent application of Pie's policies, procedures, and guidelines across multiple operational departments. This role supports and executes quality audit programs, contributes to training content development and delivery, and helps maintain the documentation and governance infrastructure that keeps our teams accurate, compliant, and improving over time. How You’ll Do It Within the framework of the department’s Quality Program, conducts...

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 Vendor Management & Sourcing Specialist is the operational backbone of Pie’s Claims Vendor Management and Procurement function, owning end-to-end work across both sourcing/procurement execution and vendor relationship and performance management. In this senior individual contributor role, you will lead the full sourcing lifecycle by translating business needs into RFx processes, conducting market research, spend analysis, benchmarking, and competitive bid evaluations, and delivering data-backed vendor selection recommendations. You will also manage the Claims...

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 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 —...