RVP, Enterprise Sales - Midwest Territory

At Sword, we’re building AI to heal billions and unlock humanity’s full potential. In doing so, we’re pioneering AI Care, a fundamentally new approach to healthcare built for medical reasoning, safety, and real-time treatment, not generic technology applied after the fact. As both a clinical-centric frontier AI lab and an applied AI platform, Sword is reimagining how care is delivered at scale, removing traditional barriers like appointments, waiting rooms, and stigma so more people can access the care they need—and ultimately get back to lives lived in full. Since 2020, Sword has expanded across physical therapy, women’s health, cardiometabolic, and mental health, and is now moving beyond the session to a fully AI-native, 24/7 care program that brings physical activity, therapeutic exercise, psychotherapy, nutrition, and behavior change into one connected experience. More than 700,000 members across three continents have completed over 10 million AI sessions, helping 1,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies, 44+ patents, and more than $500 million raised from leading investors including Khosla Ventures, General Catalyst, and Founders Fund, Sword is defining a new standard for healthcare. The Regional Vice President, Enterprise Sales Representative is responsible for driving new employer partnerships with enterprise organizations (1,000–10,000 employees) across the Northeast. This role focuses on selling Sword Health’s AI-powered care platform to benefits leaders by demonstrating measurable cost reduction, clinical outcomes, and high employee engagement. You’ll be part of Sword’s Commercial Sales team, working cross-functionally with Business Development, Clinical, Consultant Relations, and Customer Success. The team is focused on helping employers reduce healthcare costs while delivering high-quality, outcomes-driven care to their workforce. 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.