Training and Development Manager

Summary

Join Sidecar Health, a company redefining health insurance, as their Training & Development Manager. You will design, develop, and deliver training programs across various departments, including Claims, Provider Engagement, People Ops, Compliance, Legal, Sales, and Marketing. This role involves administering the Learning Management System (LMS), identifying skill gaps, translating process changes into training content, and facilitating training sessions. You will also maintain compliance training cycles, collaborate on company-wide learning initiatives, and monitor training effectiveness. The ideal candidate has 5+ years of experience in training and development, proven success in designing and delivering training programs, and hands-on LMS administration experience. Sidecar Health offers a market-based approach to compensation, with an expected salary range of $90,000-$100,000.

Requirements

• 5+ years of experience in training, learning & development, or enablement roles with increasing levels of responsibility, ideally supporting multiple departments or functions
• Proven success in designing and delivering training programs at scale , incorporating both live and asynchronous modalities
• Hands-on LMS administration experience ; direct experience with Sana LMS is a strong plus
• Strong grasp of instructional design principles, adult learning theory, and knowledge-to-training translation
• Demonstrated analytical capability to measure training impact and improve learning outcomes through data
• Exceptional communication and stakeholder engagement skills , able to collaborate across Ops, People, Compliance, and Legal teams
• Self-starter who thrives in dynamic environments , with the ability to manage multiple high-priority initiatives simultaneously

Responsibilities

• Design, develop, and deliver scalable training programs aligned with organizational goals, onboarding needs, compliance requirements, and professional development objectives
• Administer the LMS, managing course assignments, completions tracking, reporting, and maintenance of training records
• Partner closely with leaders across Claims, Provider, People Ops, Compliance, Legal, Sales, and Marketing to identify skill gaps and enablement needs
• Translate process changes, policy updates, and operational improvements into effective training content in partnership with Knowledge Management
• Facilitate training sessions, workshops, and webinars, both live and asynchronous, to support onboarding, uptraining, and cross-functional learning needs
• Maintain compliance training cycles, collaborating with Legal and Compliance teams to ensure mandatory trainings are assigned, completed, and reported accurately
• Collaborate with People Ops on company-wide learning initiatives, including manager training, AI literacy, and leadership development programs
• Monitor training effectiveness using data and feedback mechanisms, iterating on content and delivery methods to maximize learning impact

Preferred Qualifications

Familiarity with claims operations, healthcare processes, or regulated industries preferred