Head of Enterprise Sales

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible 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 RoleSidecar Health is transforming how employers and their members experience healthcare — through transparent cash pricing, no provider networks, and meaningful cost savings. As we accelerate our enterprise growth, we are looking for a Head of Enterprise Sales to lead that charge. Reporting directly to the CEO, this individual will own our enterprise sales strategy and execution at a pivotal moment for the company, with a pipeline of national accounts already in active evaluation.What You'll DoDevelop and execute a comprehensive enterprise sales strategy to drive new business growthSet and achieve ambitious revenue targets, with a focus on net-new client acquisitionIdentify and pursue opportunities within jumbo and national employer groupsBuild and scale a repeatable, high-performing sales processBuild and maintain strong relationships with brokers, consultants, and enterprise employer clientsPartner with clients to understand their unique needs and work with internal teams to tailor solutions accordinglyServe as a trusted advisor on health plan solutions and benefits strategyStay informed about industry trends, competitor offerings, and regulatory changesCollaborate with product and marketing teams to refine offerings based on market feedback and client insightsPartner with finance, operations, and member experience teams to ensure seamless client onboarding and ongoing supportProvide input on pricing strategies, service enhancements, and value propositionsWhat You'll Bring10+ years of experience in health insurance or employee benefits sales, with a strong focus on jumbo/national employer groupsProven track record of securing enterprise clients and driving significant revenue growthStrong network within the broker/consultant community and with benefits leaders at large organizationsExceptional communication, negotiation, and relationship-building skillsDeep understanding of health plan products, self-funded and ASO models, and benefits administrationStrategic thinker with the ability to balance long-term vision and short-term executionExperience in a high-growth, entrepreneurial environment is a plusBachelor's degree requiredWhat You'll GetCompetitive salary, uncapped incentive bonus, and equity package Comprehensive Medical, Dental, and Vision benefitsA 401k retirement planPaid vacation and company holidaysOpportunity 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.Originally posted on Himalayas