Operations Training Specialist, Contact Center

🕒 May 10

🇺🇸 United States – Remote

💵 $65k - $75k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

📞 Call Center Representative

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Sidecar Health

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2018

⚕️ Healthcare Insurance

Healthcare Insurance

Sidecar Health is a health insurance company that provides comprehensive major medical insurance with upfront pricing and no network restrictions or referral requirements. Their goal is to put employees in control of their healthcare by giving them a clear budget for care and allowing them to choose any doctor without surprise costs. They emphasize access to prescriptions without limitations and protection for unplanned care. Sidecar Health also offers transparent pricing and the option for members to save money if they find providers who charge less than their plan pays. Their offerings include individualized access plans and employer plans, ensuring members always have a choice of qualified doctors.

📋 Description

• 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 • 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

• 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.