Enterprise Account Executive, Health Systems

What You’ll Do

Build Pipeline and Open Strategic Accounts

• Develop and execute a named-account strategy focused on regional and national health systems
• Create net-new pipeline through outbound prospecting, executive networking, events, referrals, and strategic account activation
• Build relationships with operational and technology stakeholders across patient access, ambulatory operations, contact centers, digital transformation, IT, and executive leadership
• Multi-thread effectively across Operations, IT, Security, Finance, Procurement, and Executive sponsors

Drive Complex Enterprise Deals

• Own the full enterprise sales cycle from initial outreach through signed agreement and rollout planning
• Lead discovery, ROI analysis, solution positioning, pilots, procurement, legal review, and executive alignment
• Run disciplined deal processes with clear next steps, stakeholder mapping, and Mutual Action Plans
• Navigate InfoSec, HIPAA, procurement, and governance reviews with urgency and professionalism

Partner Cross-Functionally

• Work closely with Product, Solutions, and Leadership teams to shape implementation strategy and ensure successful deployments
• Help refine positioning, packaging, pricing, and enterprise messaging based on market feedback
• Bring structured insight on competitive dynamics, ICP expansion, and operational workflows emerging across the market

What We’re Looking For

Core Requirements

• 7–12 years of experience in enterprise healthcare sales
• Strong track record of selling into health systems, IDNs, or large provider organizations
• Experience closing complex enterprise software or services deals with multi-stakeholder buying committees
• Proven ability to self-source pipeline and open strategic accounts from scratch
• Comfortable navigating long enterprise cycles while maintaining urgency and deal momentum
• Excellent executive communication and presentation skills

Preferred Experience

• Experience in patient access, contact center, scheduling, revenue cycle, or healthcare operations
• Familiarity with major healthcare technology ecosystems including Epic, Oracle Health/Cerner, athenahealth, Genesys, NICE, Five9, or Cisco
• Experience selling AI, workflow automation, or operational technology into healthcare organizations
• Strong understanding of operational KPIs such as abandonment rate, wait times, scheduling conversion, staffing utilization, and call-center performance metrics
• Experience managing pilots and outcome-based enterprise deployments tied to measurable ROI

Traits That Matter at Prosper

• Builder mentality: excited to create the playbook, not inherit one
• High agency and accountability
• Strong operational rigor and disciplined execution
• Curious, competitive, and resilient
• Comfortable operating in fast-moving startup environments
• Motivated by winning large, strategic customers and helping shape a category