Regional Vice President of Sales, ASO - Remote

Overview

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.

In Short

• 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

Requirements

• 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

Benefits

• 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.