RVP, Enterprise Sales - Midwest Territory

What you'll be doing

• Own the full sales cycle for enterprise employers in the Northeast, from initial discovery through close including upsell opportunities with existing customers;
• Build trusted relationships with HR, Benefits, and Total Rewards leaders at self-insured employers;
• Partner closely with brokers, consultants, and health plan partners to create strong referral pipelines and facilitate contracting pathways;
• Lead discovery conversations to understand employer healthcare spend, MSK challenges, and benefits strategy;
• Articulate Sword’s differentiated value around clinical outcomes, outcomes-based pricing, and claims-based ROI;
• Coordinate and deliver executive-level presentations, live demos, and ROI analyses with internal clinical and health economics teams;
• Manage a healthy pipeline of opportunities and forecast accurately against quarterly and annual targets;
• Stay informed on competitive dynamics (e.g., Hinge, Omada) and position Sword effectively in competitive evaluations;
• Collaborate with Customer Success to ensure smooth implementations and long-term partnership success.

What you need to have

• 5+ years of experience selling into employers, preferably in healthcare, digital health, or employee benefits;
• Proven success managing complex, consultative sales cycles with HR and benefits decision-makers;
• Experience working with brokers, consultants, or health plan partners in the benefits ecosystem;
• Strong understanding of self-insured employer healthcare dynamics and cost drivers;
• Ability to clearly communicate clinical, financial, and ROI-based value to executive audiences;
• Comfort navigating competitive sales environments and differentiating on outcomes, not just features;
• Excellent organizational, pipeline management, and forecasting skills;
• Experience using CRM tools and sales enablement platforms;
• Ability to travel within the Northeast territory as needed.