RVP, Enterprise Sales - Midwest Territory

• 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.

• 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.