Enterprise Account Executive – Healthcare

Job Summary

We are seeking an experienced Enterprise Account Executive to drive new business development and strategic growth within the healthcare market. This role is responsible for identifying, developing, and closing complex enterprise opportunities with health systems and other large healthcare organizations.

The ideal candidate is a strategic, resilient, and highly motivated sales professional who is comfortable navigating long sales cycles, engaging executive stakeholders, and building customized solutions around measurable business outcomes. This is a high-ownership role for someone who can create opportunities, develop compelling business cases, and successfully manage complex, multi-stakeholder sales processes from initial prospecting through close.

Key Responsibilities

Enterprise Sales & Business Development

• Own the full enterprise sales lifecycle, from prospecting and initial outreach through contract negotiation and close.
• Develop and execute strategic account plans targeting health systems and other large healthcare organizations.
• Generate new opportunities through proactive outbound prospecting, relationship development, networking, and executive engagement.
• Build and maintain a strong enterprise pipeline while consistently prioritizing high-value opportunities.
• Navigate complex, multi-stakeholder sales processes involving executive, operational, clinical, human resources, and financial leaders.
• Manage extended sales cycles while maintaining momentum, engagement, and strong relationships throughout the process.

Executive & Stakeholder Engagement

• Establish relationships with C-suite and senior-level stakeholders, including CEOs, CFOs, COOs, CHROs, and other organizational leaders.
• Lead discovery conversations to understand organizational challenges, workforce needs, operational priorities, and business objectives.
• Build consensus among diverse stakeholders and guide prospects through complex decision-making processes.
• Present compelling solutions and business cases that clearly communicate value, ROI, and measurable outcomes.

Solution Development & Consultative Selling

• Develop customized solutions in collaboration with internal subject-matter experts and cross-functional teams.
• Translate customer challenges into practical solutions aligned with organizational goals.
• Focus sales conversations on business outcomes, operational improvements, financial impact, and return on investment rather than product features alone.
• Develop tailored proposals, presentations, business cases, and value propositions for enterprise prospects.
• Continuously refine sales strategies and messaging based on customer feedback, market conditions, and deal outcomes.

Pipeline & Deal Management

• Maintain accurate pipeline forecasts and sales activity within CRM systems.
• Qualify opportunities effectively and prioritize accounts based on strategic value and likelihood to close.
• Develop and execute deal strategies for complex enterprise opportunities.
• Lead negotiations and coordinate internal resources to move opportunities through the sales process.
• Identify risks, obstacles, and decision-making barriers and develop strategies to overcome them.
• Consistently meet or exceed enterprise sales targets and revenue objectives.

Market & Business Development

• Develop a strong understanding of the healthcare market, including workforce challenges, organizational priorities, and industry trends.
• Use market intelligence and customer insights to identify new opportunities and strengthen sales strategies.
• Represent the organization professionally at industry events, conferences, and networking opportunities.
• Provide feedback to leadership and cross-functional teams regarding customer needs, market trends, competitive positioning, and opportunities for improvement.

Qualifications

• 7+ years of progressive enterprise sales experience, preferably selling complex services or high-value solutions.
• Demonstrated success closing complex, multi-stakeholder enterprise deals with long sales cycles.
• Experience selling into healthcare organizations, health systems, hospitals, or related healthcare environments strongly preferred.
• Proven ability to engage and influence C-suite and senior executive stakeholders.
• Strong business acumen with the ability to develop compelling business cases focused on financial and operational outcomes.
• Demonstrated ability to manage lengthy and complex sales cycles while maintaining urgency and momentum.
• Strong consultative selling, discovery, negotiation, and deal-management skills.
• Exceptional written, verbal, and presentation skills.
• Ability to simplify complex concepts and communicate value effectively to both technical and non-technical audiences.
• Highly self-motivated and comfortable working independently in an entrepreneurial, high-growth environment.
• Demonstrated resilience, persistence, and ability to overcome obstacles throughout the sales process.
• Strong CRM and sales technology proficiency.

Preferred Qualifications

• Experience selling complex workforce, professional services, education, technology, healthcare, or other high-value solutions.
• Established relationships with healthcare executives and decision-makers.
• Experience selling to integrated delivery networks (IDNs), hospital systems, or large healthcare employers.
• Experience with consultative or solution-based enterprise sales.
• Experience developing ROI models, financial analyses, or executive-level business cases.