Executive Director, Enterprise Health Sales

RiseMe; United States; Hybrid; USD 180,000 - 250,000; Full time

Benefits offered by this job

Generous commission plan

Eligible for equity

99% employer paid health benefits (Med

Job summary

Regard is seeking an Executive Director to lead strategic sales to major health systems across the US. You’ll own the full sales cycle from initial outreach to contracting, craft compelling business cases, and manage a portfolio of enterprise accounts. Travel about 30% and collaborate with cross‑functional teams to drive ROI.

You will engage CFOs, CMIOs, COOs and CIOs, building consensus among finance and clinical leadership while advancing the buyer journey with purpose and precision.

Qualifications

• 5+ years selling software to major health systems with full sales cycle experience.
• Experience engaging C-suite executives (CFO, CMIO, COO, CIO) and VP-level buyers.
• Ability to build tailored business cases and multithread across executive stakeholders.
• Located within 50 miles of a major airport and willing to travel 30% of the time.

Responsibilities

• Full Sales Cycle Ownership: Own the entire sales cycle from prospecting, product demos, business case development, proposals, to contracting.
• Target Account Management: Oversee a strategic portfolio of enterprise accounts, driving activities to achieve targets and build relationships.
• Revenue Generation: Acquire, develop, and grow a base of opportunities/accounts independently.
• Consultative Selling: Understand prospect challenges and position Regard as a trusted strategic partner.
• Buyer Journey Advancement: Advance deals by purposeful meetings and project management.
• Business Case Mastery: Conduct deep discovery and create compelling business cases.
• Consensus Building: Build consensus across stakeholders including financial and clinical leadership.
• Sales Enablement: Collaborate to refine sales processes and collateral as the product evolves.
• Executive Selling: Lead strategic conversations with decision makers about investments.

Skills

Sales to health systems

C-suite engagement

Consultative selling

Strategic account management

Stakeholder alignment

Job description

Regard is seeking an Executive Director to lead strategic sales to major health systems across the US. You’ll own the full sales cycle from initial outreach to contracting, craft compelling business cases, and manage a portfolio of enterprise accounts. Travel about 30% and collaborate with cross‑functional teams to drive ROI.

You will engage CFOs, CMIOs, COOs and CIOs, building consensus among finance and clinical leadership while advancing the buyer journey with purpose and precision.