Senior Claims Learning & Development Specialist

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 Learning & Development Specialist is responsible for facilitating and supporting the design, delivery, and continuous improvement of Claims Learning & Development programs, including the creation of a Claims Skills School. This position will administer training and learning programs for workers' compensation claims, both in person and virtually, applying effective training methodologies and learning theory. The role partners closely with the Claims Quality & Compliance, Claims Adjudication, and Claims Technology teams, as well as other subject matter experts across the organization, to ensure training content reflects current processes, regulatory requirements, system capabilities, and industry best practices. How You’ll Do It Content Delivery Deliver training and facilitate learning sessions across in-person and virtual environments. Facilitate development and skill building through exercises and activities that enhance the learning process. Deliver just-in-time training and support during system implementations and process rollouts in partnership with the Claims Technology team. Adapt training delivery methods based on learner feedback and performance data to maximize retention and application. Facilitate knowledge-sharing sessions and best practice forums among claims team members. Coach and mentor new claim adjusters through their onboarding journey, including claim trainees. Program Management Collaborate with Claims leadership to identify training priorities and align learning initiatives with department goals and performance metrics. Manage the development, implementation, iteration, and measurement of claims programs such as new hire onboarding, adjuster development, Claims Skills School, and other core claims programs. Track and analyze key performance indicators related to training effectiveness such as adjuster proficiency levels, quality scores, and time to productivity for new hires. Create and maintain a knowledge base or resource library for claims processes, system guides, and reference materials. Deliver Claims All Hands presentations and communications related to learning initiatives, new programs, and skill development opportunities. Support performance review processes by providing training recommendations and development plans for claims team members. Curriculum Design Conduct training needs analyses to determine solutions to talent gaps. Create engaging learning activities and compelling course content. Design scenario-based learning modules that simulate real-world claims handling situations, including complex indemnity claims and reserve management decisions. Develop specialized training curricula for workers' compensation claim processes, including jurisdiction-specific requirements and regulations. Ensure all training materials comply with regulatory requirements, data privacy standards, and company policies. Develop competency frameworks and learning paths for adjuster development at various levels. Regularly review and update resources reflecting process changes and industry developments. Cross-Functional Collaboration Partner with the Claims Quality & Compliance team to incorporate audit findings, quality trends, and regulatory updates into training programs, ensuring training addresses identified knowledge gaps and reinforces compliance requirements. Collaborate with the Claims Adjudication team to ensure training content reflects current claim handling practices, Claims Best Practices, and operational workflows. Partner with the Claims Technology team (including the Senior Claims Application Manager and Senior Claims Business Systems Analyst) to develop and deliver end-user training for system enhancements, new features, and platform updates, ensuring training is ready at go-live. Engage with subject matter experts across Claims Operations, Regulatory Compliance, Managed Care, and Vendor Management to ensure training content reflects current processes and best practices. Support change management efforts for system rollouts, process changes, and organizational initiatives. Communication & Stakeholder Engagement Communicate effectively to a variety of audiences in both written and verbal form. Deliver complex information or new concepts in a manner conducive to learning. Develop and maintain training calendars, scheduling in-person and virtual sessions to accommodate diverse learner needs and business requirements. Follow up with Claims leadership post-training to measure effectiveness of training sessions. Report on impact of training programs to demonstrate value and inform continuous improvement. The Right Stuff High School diploma or GED required. Bachelor's degree preferred; Graduate degree (Master's, JD, or Ph.D.) preferred Minimum 8 years of related experience required. Proven experience designing and delivering training programs in a claims or insurance environment. 5+ years of experience in instructional design, curriculum development, and training delivery preferred. 8+ years of Workers' Compensation claim handling experience preferred. California jurisdiction knowledge 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. Base Compensation Range $100,000 — $125,000 USD Compensation & Benefits Competitive cash compensation A piece of the pie (in the form of equity) 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 #LI-REMOTE #BI-REMOTE