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.

Role

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.

• 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.

*This range includes base, variable and equity.

These compensation bands are just the starting point. Once someone joins and proves they’re outlier talent, we adjust quickly to ensure their compensation aligns with their impact.

Our job titles may span more than one career level. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors. Compensation details listed in this posting reflect the base salary and any potential variable, bonus or sales incentives, and the Company’s estimation of the value of private company stock options, if applicable. The pay range is subject to change, future value of company stock options is not guaranteed, and compensation may be modified in the future. In addition to our total compensation, Sword offers a number of benefits as listed below.

US - Sword Benefits & Perks:

• Comprehensive health, dental and vision insurance*

• Life and AD&D Insurance*

• Financial advisory services*

• Supplemental Insurance Benefits (Accident, Hospital and Critical Illness)*

• Health Savings Account*

• Equity shares*

• Discretionary PTO plan*

• Parental leave*

• 401(k)

• Flexible working hours

• Remote-first company

• Paid company holidays

• Free digital therapist for you and your family

*Eligibility: Full-time employees regularly working 25+ hours per week

Note: Applicants must have a legal right to work in the United States, and immigration or work visa sponsorship will not be provided.

SWORD Health, which includes SWORD Health, Inc. and Sword Health Professionals (consisting of Sword Health Care Providers, P.A., SWORD Health Care Providers of NJ, P.C., SWORD Health Care Physical Therapy Providers of CA, P.C.*) complies with applicable Federal and State civil rights laws and does not discriminate on the basis of Age, Ancestry, Color, Citizenship, Gender, Gender expression, Gender identity, Gender information, Marital status, Medical condition, National origin, Physical or mental disability, Pregnancy, Race, Religion, Caste, Sexual orientation, and Veteran status.