Head of Enterprise Sales

Sidecar Health

. Develop and execute a comprehensive enterprise sales strategy to drive new business growth .

Posted 3/30/2026full-timeRemote • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

Develop and execute a comprehensive enterprise sales strategy to drive new business growth
Set and achieve ambitious revenue targets, with a focus on net-new client acquisition
Identify and pursue opportunities within jumbo and national employer groups
Build and scale a repeatable, high-performing sales process
Build and maintain strong relationships with brokers, consultants, and enterprise employer clients
Partner with clients to understand their unique needs and work with internal teams to tailor solutions accordingly
Serve as a trusted advisor on health plan solutions and benefits strategy
Stay informed about industry trends, competitor offerings, and regulatory changes
Collaborate with product and marketing teams to refine offerings based on market feedback and client insights
Partner with finance, operations, and member experience teams to ensure seamless client onboarding and ongoing support
Provide input on pricing strategies, service enhancements, and value propositions

Requirements

What you’ll need

10+ years of experience in health insurance or employee benefits sales, with a strong focus on jumbo/national employer groups
Proven track record of securing enterprise clients and driving significant revenue growth
Strong network within the broker/consultant community and with benefits leaders at large organizations
Exceptional communication, negotiation, and relationship-building skills
Deep understanding of health plan products, self-funded and ASO models, and benefits administration
Strategic thinker with the ability to balance long-term vision and short-term execution
Experience in a high-growth, entrepreneurial environment is a plus
Bachelor's degree required

Benefits

Comp & perks

Competitive salary, uncapped incentive bonus, 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.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

health plan productsself-funded modelsASO modelsbenefits administrationenterprise sales strategyrevenue growthclient acquisitionpricing strategiesservice enhancementsvalue propositions

Soft Skills

communication skillsnegotiation skillsrelationship-building skillsstrategic thinkingcollaborationclient partnershipadaptabilityproblem-solvingleadershipnetworking

Certifications

Bachelor's degree