Enterprise Account Executive

Company: DirectShifts
‍Location: 1441 Broadway, Suite 6023, New York, NY 10018 (Preferred onsite with occasional hybrid)
‍Schedule: Monday – Friday, 9:00 AM to 5:00 PM EST
‍Compensation: Up to $120,000

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.
Role Overview
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.
This is a true enterprise sales role. You will be responsible for identifying, developing, and closing strategic partnerships with healthcare organizations. You will own the entire sales cycle—from prospecting through contract execution—and help establish DirectShifts as the leading provider operations platform. 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, targeting key healthcare organizations and building relationships with executive decision-makers. Generate new business opportunities through outbound prospecting, referrals, networking, and partnerships.

• Enterprise Sales: Own the complete sales cycle, conduct executive discovery meetings, and recommend tailored solutions to operational challenges. Deliver compelling presentations, customized proposals, and ROI analyses to negotiate and close enterprise contracts.

• Strategic Account Management: Build trusted executive relationships, ensure successful customer onboarding alongside the operations team, and drive cross-selling and upselling opportunities.

• Sales Operations: Maintain CRM accuracy, manage pipeline reporting, collaborate on marketing campaigns, and leverage AI tools for prospecting and engagement.

Key Performance Indicators (KPIs)

• 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% and CRM hygiene above 95%.

The Ideal Candidate

We are looking for a highly competitive, entrepreneurial candidate who thrives in a startup environment and takes ownership of their results.

Required Experience:

• 5-10+ years of enterprise sales experience with proven success selling six-figure and seven-figure enterprise contracts.

• Experience selling complex B2B solutions into hospitals, health systems, physician groups, digital health companies, or healthcare technology organizations.

• Strong executive presentation, negotiation, and communication skills, with experience managing long sales cycles.

Preferred Qualifications:

• Existing relationships with executive buyers such as CEOs, COOs, CMOs, CHROs, CNOs, or VPs of Talent Acquisition and Workforce Planning are strongly preferred.

• Industry experience selling Healthcare Staffing, MSP/RPO, Credentialing, Revenue Cycle Management, Healthcare SaaS, Telehealth, or Workforce Management.