Account Executive, Mid-Market Health Systems

About the role

We are seeking a motivated Account Executive to grow Cinnamon’s presence among mid-market and regional health systems. This role owns the full sales cycle, including prospecting, discovery, product demonstrations, proposals, negotiation, and close. You will work with healthcare leaders to understand their operational challenges and demonstrate how Cinnamon can streamline financial assistance workflows, reduce administrative burden, and improve patient outcomes. The ideal candidate is a proactive, organized healthcare seller who can build relationships, manage multiple opportunities, and consistently achieve revenue goals.

What you'll do

• Own the sales cycle for mid-market and regional health system opportunities, from initial outreach through contract execution.
• Conduct discovery with revenue cycle, patient access, pharmacy, finance, and operational stakeholders.
• Clearly communicate Cinnamon’s value and connect platform capabilities to customer needs.
• Deliver effective product demonstrations, presentations, proposals, and follow-up materials.
• Manage pricing discussions, negotiations, and contracting in partnership with leadership.
• Build pipeline through outbound prospecting, referrals, industry events, marketing-generated leads, and targeted account outreach.
• Consistently develop new relationships and generate qualified sales opportunities.
• Manage multiple active opportunities while maintaining clear next steps and consistent follow-up.
• Keep CRM records, pipeline stages, activity, and forecasts accurate and current.
• Meet or exceed established pipeline, activity, and revenue goals.
• Develop relationships with operational leaders and key decision-makers throughout the sales process.
• Partner with Product, Implementation, Patient Operations, and Marketing to answer customer questions and develop appropriate solutions.
• Set clear customer expectations and ensure a smooth handoff to the implementation team.
• Share recurring customer feedback, objections, and market insights with internal teams.
• Support a consistent and positive customer experience from first conversation through close.

What we're looking for

• 3–5+ years of B2B sales experience, preferably within healthcare technology, revenue cycle, patient access, pharmacy, or healthcare services.
• Experience managing a full sales cycle and meeting revenue goals.
• Familiarity with hospitals, regional health systems, or other healthcare organizations.
• Strong discovery, presentation, relationship-building, and negotiation skills.
• Ability to explain technology and operational value clearly to different audiences.
• Organized and disciplined approach to pipeline management and follow-up.
• Comfortable managing multiple opportunities in a fast-paced environment.
• Experience working with CRM and sales enablement tools.
• Ability to travel for customer meetings, conferences, and company events as needed.