Founding Senior Account Executive

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’re backed by top investors including Y Combinator (Airbnb, Coinbase) and Emergence Capital (Salesforce, Zoom), trusted by innovative healthcare organizations, and are reshaping a $4T industry.

The Role:

We’re looking for a high-performing Senior Account Executive to drive growth across healthcare providers, medical billing companies and pharmacy hubs. You’ll own the sales process end-to-end, with support from product and engineering to win deals fast. You’re proactive, product-curious, and thrive in early-stage, high-velocity environments.

**The role is 100% in person in New York City**

What You’ll Do:

• Build and close a pipeline of 5–6 figure deals
• Drive outbound prospecting with SDRs and Marketing, and run targeted outreach campaigns
• Lead discovery, demos, pilots, and negotiation—owning the full sales cycle
• Translate Prosper’s AI capabilities into clear ROI stories for billing teams and executives
• Partner with Product to close feedback loops and influence roadmaps based on customer needs

What We’re Looking For

• 3–8+ years of B2B sales experience, ideally in healthcare, SaaS, or AI
• Proven track record of closing enterprise deals
• Excellent communication, presentation, and negotiation skills
• Ability to manage multiple stakeholders and cross-functional initiatives
• Strong communicator with the ability to sell both vision and execution
• Comfortable building your own pipeline and working autonomously

Bonus Points

• Experience selling AI, automation, or voice tech
• Familiarity with EHRs, medical billing systems, or prior authorization workflows
• Networks within medical billing/RCM companies or hospital billing departments
• Background in fast-growing startups or high-ownership roles

Why Prosper

• Early traction with real customers and revenue
• Huge market opportunity in a broken industry
• Competitive comp + uncapped commission + equity
• Fast-moving team with high trust and ownership

Compensation range:

• NYC Base Salary Range: $100,000 - $150,000 USD + equity & benefits
• OTE: $200,000 - $300,000 USD (50/50 Split)

Interview Process

The interview processes is a sequence of meetings with our executive leadership team. The first step is an introductory call with our recruiter to introduce candidates to the process, share more about Prosper AI, and hear more about their experience and professional interests.

Next is a conversation with our Operations Lead, followed by another session with our Co-Founder. We then ask candidates to conduct a case study based on a prompt from the Prosper team. Once completed, we invite candidates onsite to present their case study and engage in a thoughtful conversation with our executive leadership team. Next step… an offer to join Prosper AI!