Operations Training Specialist, Contact Center

Sidecar Health

Operations Training Specialist managing training lifecycle for operations teams at Sidecar Health. Focused on onboarding, content creation, and aligning knowledge with operational changes for an enhanced member experience.

Posted 5/10/2026full-timeRemote • 🇺🇸 United StatesMid-LevelSenior💰 $65,000 - $75,000 per yearWebsite

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
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 opportunity 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.

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

instructional designtraining program developmentcontent creatione-learning modulesknowledge managementtraining effectiveness evaluationproject managementtime managementadult learning methodologiesAI-assisted content development

Soft Skills

clear communicationproactive approachcollaborationownershiporganizational skillsability to manage multiple workstreamsfeedback incorporationfacilitation skillsadaptabilityproblem-solving

Certifications

Bachelor's degree