Head of Enterprise Sales
Sidecar Health
full-time
Posted on:
Location Type: Remote
Location: United States
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Job Level
About the role
- 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
- 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
- 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.
Applicant Tracking System Keywords
Tip: use these terms in your resume and cover letter to boost ATS matches.
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