Enterprise Account Executive

About DirectShifts
DirectShifts is a rapidly growing healthcare technology company transforming provider operations for hospitals, health systems, physician groups, and digital health companies across the United States.
Our platform helps healthcare organizations recruit providers, manage state licensing, credentialing, scheduling, telehealth operations, internal resource pools (IRPs), float pools, and workforce management through a single strategic partner.
We're looking for a high-performing Enterprise Account Executive to help build the next phase of our growth. This is a rare opportunity to work directly with the CEO and become the company's first enterprise sales leader.

Role Overview
This is a true enterprise sales role.
You will be responsible for identifying, developing, and closing strategic partnerships with healthcare organizations across the United States.
You will own the entire sales cycle—from prospecting through contract execution—and help establish DirectShifts as the leading provider operations platform for healthcare organizations.
This is not a transactional staffing sales role. We are looking for a consultative seller capable of selling complex operational solutions with annual contract values ranging from $100,000 to over $1 million.
As the company grows, this individual will have the opportunity to help build and lead the enterprise sales organization.

What You'll Sell
You will represent DirectShifts' complete suite of provider operations solutions, including:
Provider Recruitment
Recruitment as a Service
State Licensing
Credentialing
Provider Scheduling
Telehealth Operations
Internal Resource Pool (IRP) Programs
Float Pool Management
Provider Operations Outsourcing
Enterprise Workforce Solutions

Key Responsibilities
Enterprise Business Development
Develop and execute a strategic territory plan.
Identify and target hospitals, health systems, physician groups, digital health companies, and healthcare organizations.
Build relationships with executive decision makers.
Generate new business opportunities through outbound prospecting, referrals, networking, conferences, partnerships, and existing relationships.
Work closely with marketing to convert inbound demand into qualified opportunities.

Enterprise Sales
Own the complete sales cycle from prospecting through contract execution.
Conduct executive discovery meetings.
Understand customer operational challenges and recommend tailored solutions.
Deliver compelling executive presentations and product demonstrations.
Develop customized proposals, pricing models, and ROI analyses.
Negotiate commercial agreements.
Close enterprise contracts.
Maintain accurate sales forecasts.

Strategic Account Management
Build trusted executive relationships.
Identify opportunities to expand existing customer relationships.
Collaborate with operations to ensure successful customer onboarding.
Drive cross-selling and upselling opportunities.

Sales Operations
Maintain CRM accuracy.
Manage pipeline reporting.
Collaborate with marketing on campaigns and messaging.
Work directly with the CEO on strategic accounts.
Leverage AI tools for prospecting, research, proposal generation, and customer engagement.

Key Performance Indicators
Annual Success Metrics
Close $2M–3M in new Annual Contract Value (ACV).
Build a healthy multi-million-dollar qualified pipeline.
Consistently exceed quarterly sales targets.
Maintain forecast accuracy above 90%.
Maintain CRM hygiene above 95%.

Ideal Candidate
We are looking for someone who has successfully sold complex B2B healthcare solutions to executive buyers.
Required Experience
5–10+ years of enterprise sales experience.
Proven success selling six-figure and seven-figure enterprise contracts.
Experience selling into hospitals, health systems, physician groups, digital health companies, or healthcare technology organizations.
Strong executive presentation and negotiation skills.
Experience managing long enterprise sales cycles.
Excellent communication skills.
Entrepreneurial mindset.

Preferred Relationships
Candidates with existing relationships among the following buyers will be strongly preferred:
Chief Executive Officers (CEOs)
Chief Operating Officers (COOs)
Chief Medical Officers (CMOs)
Chief Human Resources Officers (CHROs)
Chief Nursing Officers (CNOs)
Vice Presidents of Talent Acquisition
Vice Presidents of Workforce Planning
Medical Group Executives
Digital Health Founders
Healthcare Private Equity portfolio companies

Preferred Industry Experience
Experience selling one or more of the following:
Healthcare Staffing
MSP / RPO
Provider Recruitment
Credentialing
State Licensing
Revenue Cycle Management
Healthcare SaaS
Workforce Management
Telehealth
Provider Operations
Healthcare BPO

Leadership Characteristics
The ideal candidate:
Thinks like an entrepreneur.
Is highly competitive.
Builds executive relationships quickly.
Is comfortable selling to CEOs and executive teams.
Thrives in a startup environment.
Is coachable.
Takes ownership of results.
Uses data to improve performance.