Training & Development Manager

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen. The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent. If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

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.

Compensation

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.

Company Information

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability.