Enterprise Sales Executive - Healthcare AI

N-21.ai is seeking a high-performing, entrepreneurial Enterprise Sales Executive – Healthcare AI to help build our U.S. healthcare business. This is a hunter role. We are looking for someone who can open doors at healthcare enterprises, engage senior executives, identify high-value business problems, develop compelling Agentic AI solutions, and turn those opportunities into paid pilots, enterprise deployments, and multi-year relationships. The successful candidate will sell N-21.ai's Chiral Agentic AI Platform, AI solutions, and AI-enabled services across healthcare and selected Life Sciences organizations. Company Overview:We are an early-stage healthcare AI startup building agentic AI–driven managed outcomes platforms for Medicare Advantage and Medicaid. Our focus is on improving clinical outcomes, reducing medical costs, and driving operational efficiency for payers and risk-bearing providers. The company operates at the intersection of AI, risk adjustment, value-based care, and managed care economics. Core Mandate:Build and scale N-21.ai's U.S. healthcare enterprise business by acquiring lighthouse customers, creating a repeatable enterprise sales motion, and converting high-value Agentic AI opportunities into paid pilots, production deployments, and multi-year customer relationships. Why This Role Matters:Healthcare organizations are moving from AI experimentation to AI execution—deploying AI into complex business, administrative, clinical, and operational workflows. This role will be one of the key commercial leaders responsible for turning that market opportunity into actual enterprise adoption. Key Responsibilities:Develop new business across health plans, Medicare Advantage plans, Medicaid MCOs, provider-sponsored plans, health systems, physician organizations, value-based care organizations, and healthcare services companies.Lead executive conversations focused on business outcomes, ROI, operational transformation, and strategic value, rather than product features alone.Collaborate with product, solutions, clinical, and technical teams to translate business problems into viable AI opportunities.Develop compelling solution narratives and business cases around revenue growth, cost reduction, productivity, compliance, audit readiness, data accuracy, workflow efficiency, and engagement.Ensure pilots demonstrate measurable business value and create a clear path to enterprise-scale adoption.Own discovery, solution development, business case, proposal, pricing, procurement, security review, negotiation, close, and expansion.Maintain disciplined pipeline management, forecasting, and opportunity progression. What We're Looking For:3–5+ years of enterprise sales or business-development experience.Proven success selling complex enterprise solutions with meaningful contract values.Strong U.S. healthcare relationships and an established executive network.Experience selling into health plans, managed care organizations, providers, or healthcare services organizations.Demonstrated ability to independently prospect, create opportunities, manage complex sales cycles, and close enterprise deals.Strong executive communication, consultative selling, negotiation, and business-development skills.Ability to work effectively with founders, product, technical, clinical, and solutions teams.Experience or domain knowledge in one or more of Medicare Advantage, Medicaid Managed Care, Risk Adjustment / RADV, Value-Based Care, HEDIS / Quality / Stars, Payment Integrity, Utilization Management, Population Health, Member Engagement, Healthcare Analytics, Clinical Operations, AI / Data / Analytics / SaaS, Healthcare Technology or Consulting.Comfortable working directly with founders and taking ownership without extensive structure. Success Metrics:First 90 Days1. Build a prioritized target-account list across key healthcare segments.2. Activate and leverage a strong U.S. healthcare executive network.3. Create approximately 10–15 meaningful enterprise opportunities.4. Establish several qualified paid-pilot opportunities.5. Develop strong fluency in the Chiral Agentic AI Platform and priority healthcare use cases.First 6 Months1. Build $3M–$5M+ in qualified pipeline.2. Secure initial lighthouse customers and paid pilots.3. Establish a repeatable and scalable enterprise sales motion.4. Develop executive relationships that create opportunities for enterprise expansion.First 12 Months1. Deliver $1.0M–$1.5M+ in new ACV, depending on territory and deal structure.2. Successfully convert pilots into production deployments.3. Establish referenceable healthcare customers.4. Drive expansion across multiple use cases and business workflows.5. Maintain 3–4× forward pipeline coverage.Overall Success1. Consistently generate new enterprise healthcare opportunities.2. Convert opportunities into paid pilots and production deployments.3. Build long-term, multi-year enterprise relationships.4. Expand customer adoption of Chiral across multiple use cases.5. Establish a repeatable healthcare enterprise sales engine.