Enterprise Sales Executive (AI Native)

Accountabilities:: Build trusted relationships with hospitals, health systems, surgical centers, home health organizations, and post-acute care providers to develop new enterprise partnerships. Own the full sales cycle within an assigned territory, from prospecting and relationship development through negotiation, closing, and expansion. Lead consultative solution-based sales processes involving multiple C-suite decision-makers, influencers, and cross-functional teams within complex healthcare organizations. Develop and communicate compelling value propositions tailored to customer priorities, business challenges, and healthcare workforce needs. Navigate AI governance boards, IT stakeholders, integration requirements, and other technical or organizational considerations involved in enterprise adoption. Build, maintain, and actively manage a robust sales pipeline through strategic prospecting, networking, and account development. Partner closely with Marketing and Customer Success to accelerate territory growth, support customer expansion, and contribute to broader commercial objectives. During the first six months, become highly proficient in communicating the value proposition to CHRO, CNO, and CEO audiences, generate and close new opportunities, build a 5x pipeline, and close multiple enterprise deals. Requirements 10+ years of experience selling enterprise software solutions within the healthcare industry, with a strong record of success in complex B2B sales. Experience in healthcare technology, healthcare services, or selling directly to senior executive personas such as CEOs, COOs, CHROs, and CNOs is strongly preferred. A multi-year track record of consistently achieving or exceeding sales quotas and delivering measurable commercial results. Deep experience managing complex enterprise deals involving multiple stakeholders, decision-makers, and internal influencers. Demonstrated experience using AI in day-to-day work to improve productivity, decision-making, sales effectiveness, or other key business outcomes. Ability to thrive in fast-paced, highly entrepreneurial environments while taking ownership, experimenting with new approaches, and adapting quickly. Strong consultative selling, strategic thinking, positioning, negotiation, presentation, and customer relationship skills. Ability to learn new markets quickly, stay current with industry trends, and translate market insights into actionable sales strategies. Excellent verbal and written communication skills, with confidence engaging customers, senior executives, and internal leadership. Genuine interest in marketplace technology, artificial intelligence, and emerging AI-driven business models. Benefits Competitive, market-based salary aligned with skills and experience. Commission and/or equity opportunities may be available depending on the position. 100% remote work within the eligible U.S. states. Comprehensive medical, dental, and vision coverage with shared premiums. Company-sponsored 401(k) retirement plan. Unlimited vacation to support flexibility and time away when needed. Generous family leave policy. Opportunity to work on technology and AI solutions addressing significant challenges in the healthcare workforce. High-caliber, multidisciplinary environment bringing together healthcare professionals, engineers, designers, sales leaders, account managers, and other specialists. Fast-moving, entrepreneurial culture with opportunities to influence growth strategy, new markets, and evolving products. Inclusive environment that welcomes candidates from backgrounds historically underrepresented in the industry. Strong emphasis on culture, community, collaboration, respect, and camaraderie.