Enterprise Account Executive, Health Systems

About Prosper AI

At Prosper AI, we're pioneering the most advanced conversational AI agents tailored for the healthcare industry. Since our founding, we've successfully onboarded dozens of major customers, empowering hospitals and multispecialty clinics to get paid faster and more efficiently, through streamlined revenue cycle management.

Our AI agent, Paige, handles tasks like eligibility checks, prior authorizations, claim status follow-ups, and patient scheduling, reducing costs by over 50% for medical billing teams. We’ve raised a total $35M Series A from top investors like a16z (Github, Slack), Base10 (Figma, Notion), YC (Stripe, Airbnb) and Emergence (Salesforce, Zoom). We are trusted by innovative healthcare organizations, and are reshaping a $4T industry.

About the Role

Prosper AI is building the category-defining AI workforce for healthcare operations. We are now expanding deeper into enterprise health systems and looking for an exceptional Account Executive to help lead that motion.

This is a high-ownership role for someone who wants to do more than carry a quota. You will help define how Prosper wins in large health systems: shaping our GTM strategy, landing early flagship customers, and helping turn an emerging enterprise motion into a repeatable engine.

You’ll work directly with company leadership and some of the largest healthcare organizations in the country, helping operational leaders rethink how patient access, scheduling, contact centers, and revenue cycle workflows are run in an AI-first world.

This role is ideal for someone who thrives in ambiguity, knows how to navigate complex enterprise organizations, and enjoys building from zero.

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.