Training and Development Lead

Summary

Join Sidecar Health, a company redefining health insurance, as their Training and Development Lead. Design and scale strategic learning initiatives for the Claims organization, building a strong operational foundation and driving improvements in quality and productivity. Lead end-to-end planning and execution of training projects, ensuring timely delivery and alignment with business needs. Evaluate training effectiveness, identify skill gaps, and facilitate workshops. Collaborate with cross-functional teams and stay current on L&D best practices. This role requires 3+ years of experience in training and development, expertise in instructional design, strong analytical and communication skills, and a Bachelor’s degree or equivalent experience. Sidecar Health offers a competitive salary, bonus, equity, comprehensive benefits, 401k, paid time off, and the opportunity to impact healthcare.

Requirements

• 3+ years of experience in training, learning & development, or organizational enablement
• Proven expertise in instructional design, adult learning principles, and curriculum development
• Strong analytical skills to evaluate training impact and link programs to business outcomes
• Excellent communication, facilitation, and stakeholder management skills across all levels
• Ability to lead projects independently and thrive in a fast-paced, high-growth environment
• Bachelor’s degree in Education, Organizational Development, Business, or a related field (or equivalent experience)

Responsibilities

• Design, develop, and scale strategic training programs aligned with Claims operational priorities
• Lead end-to-end planning and execution of training projects, ensuring timely delivery and alignment with business needs
• Evaluate training effectiveness through defined KPIs, continuously improving based on data and feedback
• Identify skill gaps and enablement opportunities through close partnership with Claims leadership
• Facilitate workshops and targeted upskilling sessions to drive operational excellence
• Collaborate with cross-functional teams, including Knowledge Management and Instructional Design, to deliver cohesive training solutions
• Stay current on L&D best practices to continuously innovate our approach

Benefits

• Competitive salary, 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