Strategic Health Systems Sales Leader

REGARD; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Generous commission plan

Eligible for equity

Employer-paid health benefits + One MD

18 PTO days/yr + 1 week holiday break

Annual learning stipend $750

Team retreat + social events

Sabbatical program

Job summary

Regard is seeking an Executive Director of Sales to lead strategy and execution of enterprise sales with US health systems. You will own the full sales cycle, craft tailored business cases, and build consensus among clinical and financial leaders to demonstrate ROI.

This role requires a consultative mindset, 30% travel, and the ability to advance complex buyer journeys. You will partner with Marketing, Product, and Legal to move deals from discovery to contract.

Qualifications

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

Responsibilities

• Own the entire sales cycle from prospecting to contracting.
• Oversee a strategic portfolio of enterprise accounts and hit targets.
• Acquire, develop, and grow a base of opportunities independently.
• Gain deep understanding of prospect challenges and position Regard as a strategic partner.
• Advance deals by preparing for meetings and project-managing the buyer journey.
• Conduct deep discovery and create compelling business cases.
• Build consensus across financial and clinical leadership to drive deals.
• Collaborate with Marketing, Product, and Sales leadership to refine processes.
• Lead strategic conversations with executive decision-makers.

Skills

Full Sales Cycle Ownership

Target Account Management

Revenue Generation

Consultative Selling

Buyer Journey Advancement

Business Case Mastery

Consensus Building

Sales Enablement

Executive Selling

Job description

Regard is seeking an Executive Director of Sales to lead strategy and execution of enterprise sales with US health systems. You will own the full sales cycle, craft tailored business cases, and build consensus among clinical and financial leaders to demonstrate ROI.

This role requires a consultative mindset, 30% travel, and the ability to advance complex buyer journeys. You will partner with Marketing, Product, and Legal to move deals from discovery to contract.