Sidecar Health · 2 weeks ago
Operations Training Specialist, Member Care
United States
Full-time
Remote
Mid Level
$65K/yr - $75K/yr
3+ years expSidecar Health is redefining health insurance with a mission to make healthcare affordable and accessible. The Operations Training Specialist will manage the training lifecycle for operations teams, focusing on onboarding and ongoing training to enhance team readiness and performance.
FinTechHealthcareHealth InsuranceProperty & Casualty InsuranceHealth CareInsuranceInsurTech
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
Qualification
Required
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
Benefits
Bonus and equity package
Comprehensive Medical, Dental, and Vision benefits
A 401k retirement plan
Paid vacation and company holidays
Company
Sidecar Health
Sidecar Health's employer plans empower members with transparency, control, and financial incentives to make smart healthcare decisions.
201-500 employees
Funding
Current Stage
Late StageTotal Funding
$328MKey Investors
Koch Disruptive TechnologiesDrive CapitalCathay Innovation
2024-06-26Series D· $165M
2021-01-26Series C· $125M
2020-07-23Series B· $20M
Leadership Team
Patrick Quigley
Chief Executive Officer
Sharath Pasupunuti
Chief Technology Officer
Recent News
Business Wire
2026-05-16
2026-04-04
Morningstar.com
2026-03-04
Company data provided by crunchbase