
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.
Content Delivery
Program Management
Curriculum Design
Cross-Functional Collaboration
Communication & Stakeholder Engagement
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.
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.
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.
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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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

At Pie Insurance, our mission is simple: make small business insurance affordable and as easy as pie. We specialize in workers' compensation and commercial auto insurance for small businesses across the U.S.
With our data-driven approach, small businesses can get a workers’ comp quote in just three minutes and save up to 30% on premiums.*
At Pie, culture isn’t just a buzzword; it’s what drives us. We’re obsessed with giving our customers the best experience, always curious, and never afraid to tackle challenges head-on. We believe that diversity fuels innovation and we aim to foster an inclusive environment where everyone has an opportunity for impact and growth.
🏆 Pie has been named to: Forbes’ America’s Best Startup Employers 2025, Purpose Jobs’ Best Places To Work Remote in 2025, BuiltIn's Best Places to Work in Colorado (2025), Best Remote Midsize Places to Work (2025), among others.
⚠️ Safety First ⚠️
Pie is committed to your security during the recruitment process. Verify the identity of recruiters before sharing personal or financial details. Protect yourself from job scams and report suspicious activity.
* Individual savings and quote time may vary. Discounts and savings not available for workers’ compensation policies in Wisconsin.