Regional Vice President of Sales, ASO

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September 5

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Sidecar Health

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Healthcare Insurance

Sidecar Health is a health insurance company that provides comprehensive major medical insurance with upfront pricing and no network restrictions or referral requirements. Their goal is to put employees in control of their healthcare by giving them a clear budget for care and allowing them to choose any doctor without surprise costs. They emphasize access to prescriptions without limitations and protection for unplanned care. Sidecar Health also offers transparent pricing and the option for members to save money if they find providers who charge less than their plan pays. Their offerings include individualized access plans and employer plans, ensuring members always have a choice of qualified doctors.

201 - 500 employees

Founded 2018

⚕️ Healthcare Insurance

📋 Description

• 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.