Operations Training Specialist, Member Care

About the role

The Operations Training Specialist on the Enablement team at Sidecar Health is responsible for the full training lifecycle for Sidecar Health's operations teams. This includes designing and facilitating training programs, managing logistics, and ensuring ongoing effectiveness. The role supports Member Care operations but can contribute to other teams as the business grows. The position requires a collaborative mindset, strong project and time management skills, and a proactive approach to training and knowledge management.

Responsibilities

• 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

Requirements

• 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

• 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

Pay

$65,000 - $75,000

Schedule

Full-time