Training and Development Lead - Remote

Overview

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and attainable for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

In Short

• 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

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)

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.