RVP, Enterprise Sales - Midwest Territory

AI Proficiency at Sword Health

AI fluency is a core expectation at Sword Health. Every candidate is assessed against our three-level framework — be ready to share real examples of how AI is already part of how you work.

Explorer (Level 1) — Uses AI daily to boost personal productivity

Builder (Level 2) — Creates workflows and tools that elevate the whole team

Integrator (Level 3) — Embeds AI into products and processes at scale

Every hire must demonstrate at least Level 1. The expected level will vary depending on the seniority of the role.

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.