Training and Development Lead

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.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

As Sidecar Health continues to grow, we’re seeking a Training and Development Lead to design and scale strategic learning initiatives for our Claims organization. This role is critical to building a strong operational foundation, accelerating employee development, and driving measurable improvements in quality and productivity.

What You’ll Do

• 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

What You'll Bring

• 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)

What You'll Get

• 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. 

Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.