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 facilitate ongoing refresher, upskilling, and process change training as business needs evolve
• Build and maintain all training materials for assigned teams — e-learning modules, facilitator guides, presentations, knowledge checks, role-play scenarios, and assessments
• Own operations-specific knowledge content within the knowledge management system, ensuring accuracy and alignment with current policies, workflows, and product changes
• Assess the training and knowledge impact of operational and product changes as they come through, and proactively develop or update materials to support those changes
• Manage all program logistics independently: LMS administration, scheduling, roster management, Zoom coordination, and SME preparation and briefing
• Coordinate SME and supervisor involvement in training programs — providing clear direction and session context so their contributions are set up for impact
• Evaluate training effectiveness through assessment data, QA results, nesting observations, and supervisor feedback — and act on gaps proactively
• Develop and maintain coverage plans and program documentation so training continuity is never dependent on a single person's availability
• Collaborate with the broader Enablement team on knowledge management, L&D initiatives, and operational content projects
• Use AI-assisted tools to develop content efficiently, with full accountability for review and quality of all outputs

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.