RVP, Enterprise Sales

Requirements

• 8+ years of experience in enterprise, digital health, or benefits solution sales with a strong track record of exceeding quotas.
• Proven ability to sell complex solutions into HR/Benefits departments at large employers, ideally with deal sizes over $500,000 in annual contract value.
• Deep understanding of the U.S. employer benefits ecosystem, including mental health, employee assistance programs (EAP), and wellbeing trends.
• Strong consultative selling, negotiation, and executive presence with the ability to navigate long and strategic sales cycles.
• Ability to manage multiple stakeholders, including HR, Finance, Procurement, and external brokers/consultants.
• Demonstrated ability to identify process gaps and implement improved sales methodologies that enhance team effectiveness and customer outcomes.
• Experience applying design thinking principles to sales challenges, with the ability to challenge assumptions and continuously improve sales approaches.
• Excellent communication skills—both written and verbal—and comfort developing business cases and delivering compelling presentations.
• Highly self-motivated, organized, and goal-oriented with a bias for action in a fast-paced, high-growth environment.
• Comfortable using CRM tools like Salesforce to manage pipeline and forecast accurately.

Benefits

• Base salary: $115,000-$150,000
• Quarterly variable
• Equity
• Benefits
• Annual on-target earnings: $230,000-$300,000
• Comprehensive healthcare coverage
• Monthly wellness stipend
• Retirement savings match
• Lifetime Headspace membership
• Generous parental leave