Operations Training Specialist, Member Care

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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

As an Operations Training Specialist on our Enablement team, you will own the full training lifecycle for Sidecar Health's operations teams — from building programs to running them to keeping them current and effective over time. This is a hands‑on role in every sense: you design the content, facilitate the sessions, manage the logistics, and follow through on outcomes from a new hire's first day through the point they are ready to perform independently on the floor.

Your primary focus will be supporting Member Care operations, with the scope and flexibility to contribute to additional operations teams as the business grows. You will work closely with stakeholders across Member Care, Claims, Clinical, and Provider Ops, and you will be an active contributor to a broader enablement function that spans training program management, knowledge management, and ongoing learning and development.

Your contributions will directly shape the readiness and confidence of our operations teams, equipping them with the tools, knowledge, and skills needed to deliver an outstanding member experience.

What You’ll Do:

• Own the end‑to‑end new hire onboarding experience for assigned operations teams — program design, content creation, classroom delivery, nesting coordination, job shadowing, and floor readiness evaluation
• Design and faciliti…

What You’ll Bring:

• 3+ years of experience in training, instructional design, or knowledge management, ideally within a contact center or customer service environment
• Bachelor's degree or equivalent relevant experience in a similar role
• Demonstrated end‑to‑end ownership of training programs — you have built them, run them, and improved them without requiring step‑by‑step direction
• Strong project and time management skills, with the ability to manage multiple workstreams and deadlines concurrently
• Clear and proactive communication skills, with experience delivering training sessions virtually and in person
• Familiarity with knowledge management systems, learning management systems (LMS), or other documentation tools
• Collaborative mindset, with the ability to partner across teams and departments
• A proactive, ownership‑driven approach to managing training programs and knowledge resources
• Knowledge of instructional design principles and adult learning methodologies
• Comfort with AI‑assisted content development tools and strong editorial judgment about quality and accuracy of outputs

Preferred not Required Experience:

• Experience designing or facilitating training in a contact center or call center environment — including soft skills, de‑escalation, or member/customer communication training
• Health insurance industry experience
• Experience with Sana, Document360, or similar LMS and knowledge management platforms

Why Join Us?

• Competitive salary ($65,000 ‑ $75,000) + bonus and equity package
• Comprehensive Medical, Dental, and Vision benefits
• A 401k retirement plan
• Paid vacation and company holidays
• Opportunity to make an impact at a rapidly growing mission‑driven company transforming healthcare in the U.S.

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 status.