Deputy General Counsel

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 the architect and driver of the Legal department's strategic vision at Sidecar Health, you will lead the charge in shaping a robust legal function. Your role is crucial in managing all legal, regulatory, risk, and compliance matters, contributing significantly to our company’s continued growth and operational excellence.

What You’ll Do

• Lead and mentor the legal team, fostering an environment of growth and professional development 
• Develop and implement comprehensive legal strategies to support Sidecar Health’s objectives and operational needs 
• Serve as a strategic advisor to the leadership team and board, guiding critical decision-making across legal domains including state and federal regulatory requirements and filings, litigation, employment law, compliance, enterprise risk management, and more 
• Design and oversee compliance programs across various regulatory landscapes, with a focus on insurance law, data protection, privacy laws, employment regulations, and corporate compliance 
• Manage litigation, external counsel relationships, and dispute settlements with strategic foresight 
• Provide legal support for corporate governance, M&A, and corporate finance matters, directly or through management of outside counsel 

What You’ll Bring 

• 10-15 years of experience in an in-house legal setting, preferably in a health plan 
• Proven leadership experience in fast-paced, high-growth environments, with a track record of building and mentoring effective teams 
• Strategic legal expertise in a corporate setting, with a knack for navigating complex legal and regulatory landscapes 
• Experience in the health plan sector, with demonstrated experience interacting with state regulatory agencies, regulatory filings, and compliance with state and federal insurance laws 
• Experience with market conduct examinations 
• Experience in high-growth companies, with understanding of the complexities involved in scaling operations 
• Entrepreneurial spirit, viewing ambiguity as an opportunity and thriving in dynamic environments 
• High emotional intelligence with excellent communication skills, capable of engaging effectively at all levels of the organization 
• Innovative and analytical thinking, with a bias for getting to yes, scrappy execution and a data-driven approach to decision making 
• A commitment to fostering a culture of innovation, execution, collaboration, accountability, positivity, and fun 
• Aligned with the mission to transform healthcare delivery, embodying a growth-oriented and proactive learning attitude 

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.