Enterprise Account Executive

Enterprise Account Executive – Healthcare (U.S.)

Dossier is a healthcare-focused SaaS company with over 25 years of experience helping hospitals build compliant, high-performing workforces. Trusted by leading health systems across the U.S. and Europe, our platform enables more than half a million healthcare professionals to manage and validate competencies in real time.

With deep roots in healthcare and a strong international track record, Dossier is becoming a critical system for organizations navigating workforce challenges, regulatory demands, and the shift toward AI-ready data.

As we continue to expand across the United States, we are building a high-performing enterprise sales team focused on partnering with large health systems and nursing leadership.

The Role

We’re hiring a senior Enterprise Account Executive to drive new business and expansion within large health systems across the U.S.

This is a true enterprise role, you will own complex, multi-stakeholder deals end-to-end and sell directly into nursing and executive leadership, including Chief Nursing Officers (CNOs), CIOs,CHROs, and Nursing Directors.

You will be responsible for engaging large healthcare organizations, understanding their operational and clinical needs, and positioning Dossier’s solutions to deliver measurable impact.

You’ll be expected to build pipeline, lead executive conversations, and close $100K+ ACV deals in a highly strategic sales environment.

What You’ll Do

• Own the full enterprise sales cycle from prospecting through close and expansion
• Build and manage a pipeline of large health system opportunities
• Develop relationships across clinical, operational, and executive stakeholders
• Lead discovery tied to business outcomes (quality, staffing, efficiency, risk)
• Run structured deal processes (MEDDICC preferred)
• Drive deals forward with clear next steps, mutual action plans, and compelling events
• Navigate complex procurement, IT, and implementation processes
• Maintain accurate pipeline visibility and deal progression within CRM (HubSpot)
• Partner with Customer Success to expand accounts post-sale
• Contribute to refining sales strategy as we scale

• 7+ years of enterprise SaaS sales experience
• Proven track record closing $200K+ ACV deals
• Experience selling into health systems or hospitals
• Background from Workday, UKG, or similar HRIS / LMS / workforce platforms strongly preferred
• Experience selling to executive stakeholders (CNO, CIO, CHRO, VP-level)
• Strong pipeline generation skills (not reliant on inbound)
• Experience with structured sales methodology (MEDDICC preferred)
• Skilled at multi-threading and navigating complex buying committees
• Highly disciplined in deal management and forecasting
• Comfortable operating within CRM systems (HubSpot preferred) with strong data hygiene and pipeline visibility
• Comfortable operating in a fast-paced, scaling environment with evolving processes

Nice to Have

• Existing relationships within health systems (nursing leadership, clinical education, HR, or IT)
• Experience selling workforce, HRIS, LMS, or healthcare technology
• Exposure to AI-driven platforms

• Competitive base salary with uncapped commission and strong earning potential
• Equity package included
• Comprehensive health, dental, and vision insurance
• 401(k) plan
• Fully remote role within the United States
• Opportunity to sell into large enterprise health systems
• High-impact role with visibility across leadership and ability to influence strategy
• Collaborative, performance-driven culture
• Strong growth opportunity as we scale in the U.S.