Senior Enterprise Account Executive, Health Systems

About the role

We are seeking an experienced Senior Enterprise Account Executive to lead strategic sales efforts with large and complex health systems. This role owns the full sales cycle, from developing executive relationships and identifying opportunities through proposal development, negotiation, and close. You will partner with leaders across revenue cycle, patient access, pharmacy, finance, operations, and technology to demonstrate how Cinnamon can improve financial assistance workflows and patient outcomes. The ideal candidate has a strong healthcare network, a track record of closing high-value enterprise agreements, and the ability to navigate complex health system buying processes.

What you'll do

• Own the complete sales cycle for large, complex health system opportunities, from prospecting through contract execution.
• Develop account strategies that address multiple stakeholders, facilities, service lines, and operational priorities.
• Build relationships with executive and senior leaders across revenue cycle, patient access, pharmacy, finance, operations, and technology.
• Identify health system challenges and translate them into compelling business cases for Cinnamon’s platform and services.
• Navigate lengthy procurement, security, legal, compliance, and executive approval processes.
• Build and maintain a strong pipeline of qualified enterprise health system opportunities.
• Leverage industry relationships, conferences, referrals, and targeted outreach to engage prospective customers.
• Partner with Marketing and leadership on account-based strategies for priority health systems.
• Maintain accurate opportunity data, forecasts, next steps, and account plans within the CRM.
• Consistently meet or exceed revenue and pipeline targets.
• Lead discovery conversations to understand each health system’s financial assistance programs, workflows, technology environment, and strategic priorities.
• Partner with Product, Implementation, Patient Operations, and executive leadership to develop solutions for complex customer needs.
• Deliver executive-level presentations, product demonstrations, proposals, and business cases.
• Lead pricing discussions and contract negotiations while protecting Cinnamon’s strategic and financial objectives.
• Establish clear expectations and support a smooth transition from sales through implementation.
• Bring customer and market insights back to Product, Marketing, and company leadership.
• Monitor competitive trends, health system priorities, and changes affecting patient financial access.
• Represent Cinnamon at industry conferences, executive meetings, and strategic events.
• Serve as a trusted advisor to prospective customers throughout the buying process.

What we're looking for

• 7+ years of healthcare enterprise sales experience, preferably selling technology, revenue cycle, patient access, pharmacy, or financial assistance solutions.
• Demonstrated success closing complex, high-value agreements with hospitals or health systems.
• Established relationships with health system decision-makers and influencers.
• Strong understanding of enterprise healthcare purchasing, procurement, security, legal, and contracting processes.
• Ability to communicate effectively with both executive and operational stakeholders.
• Experience building business cases and demonstrating measurable financial and operational value.
• Strong negotiation, forecasting, pipeline management, and presentation skills.
• Comfortable operating independently in a fast-moving, growth-stage company.
• Ability to travel for customer meetings, conferences, and company events as needed.