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

The Regional Vice President of Sales, ASO, will drive new business growth within Sidecar Health’s National and Strategic Accounts (NASA) segment. Reporting directly to the Market President, this is a senior-level, individual contributor sales role responsible for developing and closing new ASO (Administrative Services Only) opportunities with large, self-funded employer groups and strategic broker/consultant partners.The ideal candidate will bring deep expertise in ASO distribution, strong broker and consultant relationships, and a proven track record of selling innovative health solutions to jumbo and national accounts. This role is highly visible, entrepreneurial, and pivotal in accelerating Sidecar Health’s expansion in the employer market.

What You’ll Do

Own the full sales cycle for ASO/NASA prospects, from pipeline generation through contract execution
Cultivate and expand strategic relationships with national benefits consultants, brokers, and employer decision-makers
Drive consultative sales conversations, clearly articulating Sidecar Health’s differentiated value proposition and ROI for self-funded employers
Partner with actuarial, underwriting, product, and implementation teams to develop compelling solutions tailored to prospect needs
Deliver presentations, finalist meetings, and executive-level pitches with credibility and executive presence
Negotiate deal structures, pricing, and contracts in collaboration with leadership and legal
Consistently meet and exceed new business sales goals and revenue targets
Maintain accurate pipeline management and reporting through CRM and sales tools
Represent Sidecar Health at industry conferences, events, and networking forums to elevate brand presence and drive business development
Partner closely with the Market President, NASA, to shape go-to-market strategies and refine sales playbooks for the ASO segment

What You’ll Bring

Proven success in enterprise sales, consistently meeting or exceeding new business sales targets within ASO and self-funded employer groups
8+ years of experience selling health insurance, healthcare services, or adjacent solutions into national or jumbo accounts (10k+ lives)
Strong broker and consultant relationships, with a track record of successfully navigating distribution channels to close complex deals
Executive presence with excellent presentation, negotiation, and closing skills
Deep understanding of ASO models, healthcare cost containment strategies, and employer benefits dynamics
Ability to thrive in a fast-paced, high-growth environment, with an entrepreneurial mindset and comfort operating with ambiguity
Bachelor’s degree

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.