Offer summary

Qualifications:

3+ years of experience in training, learning & development, or organizational enablement., Proven expertise in instructional design and curriculum development., Strong analytical skills to evaluate training impact and link programs to business outcomes., Bachelor’s degree in Education, Organizational Development, Business, or a related field..

Key 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.

Evaluate training effectiveness through defined KPIs and continuously improve based on data and feedback.

Facilitate workshops and collaborate with cross-functional teams to deliver cohesive training solutions.

Job description

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.

In taking a market-based approach to compensation, base pay may vary depending on location. Additionally, base pay may vary considerably depending on job-related skills and experience. The current expected salary range for this position is: $75,000 - $90,000.

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.

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