Operations Training Specialist, Member Care

Sidecar Health

Operations Training Specialist on Enablement team at Sidecar Health. Owning training lifecycle for operations teams and facilitating their development throughout onboarding and ongoing training.

Posted 7/21/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSenior💰 $65,000 - $75,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in training program ownership, instructional design, and knowledge management within operational environments. Proficient in developing training materials and evaluating training effectiveness using data-driven insights.

Highest-signal resume keywords

Training Program OwnershipInstructional Design PrinciplesLearning Management Systems (LMS)Project ManagementAI-Assisted Content Development

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Training Program DesignContent CreationE-Learning Module DevelopmentAssessment DevelopmentKnowledge ManagementTraining Effectiveness EvaluationProcess Change TrainingFacilitator Guide CreationClassroom DeliveryNesting Coordination

Soft Skills

Clear CommunicationCollaborative MindsetProactive ApproachTime ManagementAdaptability

Tools & Technologies

Knowledge Management SystemsLearning Management Systems (LMS)ZoomAI-Assisted Tools

Industry Keywords

Contact CenterCustomer ServiceAdult Learning MethodologiesTraining LogisticsOperational Content Projects

About the role

Key responsibilities & impact

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

What you’ll need

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

Benefits

Comp & perks

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.