Senior Counsel, Group Markets

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

Sidecar Health is hiring for a Senior Counsel, Group Markets. Your primary focus will be shaping the design of group products, including self-funded and fully insured options. You will support our Sales, Operations, and Account Management teams with legal guidance on benefit design and compliance. Your expertise in ERISA, cafeteria plans, the Affordable Care Act, and employee benefits will be crucial in navigating industry complexities and ensuring we provide the best solutions for our employer customers.

What You’ll Do

• Help shape the design of group products, including self-funded and fully insured options
  
• Guide the launch of ASO (Administrative Services Only) self-funded products
• Deliver legal advice and support to Sales (Channel and Sales Operations) and Account Management (AM) on group health plan benefit design and regulatory requirements 
• Advise on regulatory requirements, including requirements related to insurance, tax, and benefits 
• Provide legal support in the negotiation and drafting of contracts and agreements related to employee benefits 
• Provide succinct, practical, and results-oriented legal advice that appropriately balances risk 
• Address and solve complex issues in a clear and concise manner

What You’ll Bring 

• Juris Doctor (J.D.) degree Required 
• 7+ years of related experience in employee benefits, ERISA, and compliance 
• Proven track record in supporting self-funded ASO offerings a plus
• Admitted to practice or eligible for in-house counsel registration 
• Excellent communication, interpersonal, and presentation skills 
• Ability to present complex issues in a clear and concise manner 
• Strong analytical thinking and problem-solving skills 
• Excellent judgment 

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.