Training and Development Manager - Sidecar Health

The Training & Development Manager will support company-wide training initiatives across a variety of departments, including Claims, Provider Engagement, People Ops, Compliance, Legal, Sales, and Marketing. This role plays a vital part in designing, delivering, and sustaining effective learning programs that empower employees to succeed, remain compliant, and grow professionally. You will also oversee the day-to-day operations of the Learning Management System (LMS), ensuring training resources are accessible, up-to-date, and impactful.

What You’ll Do

• 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 

What You’ll Bring: 

• 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 

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

• 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 

In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $90,000 - $100,000.