Head of Enterprise Health Systems Sales

Regard; Chicago (IL); Hybrid; USD 150,000 - 170,000; Full time

Benefits offered by this job

Generous commission plan

Eligible for equity

Employer-paid health benefits (Medical

Dental & Vision

18 PTO days/yr + 1 week holiday break

Annual learning stipend

Team retreat & social events

Sabbatical program

Job summary

Regard is seeking an Executive Director to lead strategy and execution of sales into large health systems across the US. You will analyze prospects' challenges, build tailored business cases, and drive consensus across clinical and financial leadership, delivering measurable ROI.

Role requires deep discovery, multithread, and travel about 30%. The company emphasizes a consultative approach and ROI-focused outcomes with enterprise-scale impact.

Qualifications

• 5+ years of experience selling software to major health systems
• Ability to engage CFOs, CMIOs, COOs, CIOs and other executives
• Experience building tailored business cases and multi-threading in complex deals
• Located within 50 miles of a major airport and willing to travel 30%+

Responsibilities

• Own the full sales cycle from prospecting to contracting
• Manage a strategic portfolio of enterprise accounts
• Acquire, develop, and grow opportunities independently
• Conduct deep discovery and build consensus across clinical and financial leadership
• Advance deals through purposeful meetings and project management
• Create compelling business cases and ROI narratives
• Collaborate with Marketing, Product, and Sales leadership to refine collateral
• Lead strategic conversations with decision makers

Skills

Sales to health systems

C-suite engagement

Consultative selling

Executive communication

Job description

Regard is seeking an Executive Director to lead strategy and execution of sales into large health systems across the US. You will analyze prospects' challenges, build tailored business cases, and drive consensus across clinical and financial leadership, delivering measurable ROI.

Role requires deep discovery, multithread, and travel about 30%. The company emphasizes a consultative approach and ROI-focused outcomes with enterprise-scale impact.