Enterprise Sales Director — Complex Deals & CWS Solutions

Lifted, an Upwork Company™; United States; Remote; USD 150,000 - 240,000; Full time

Benefits offered by this job

Medical coverage

Unlimited PTO

401(k) with matching

Parental leave (12 weeks)

Sales incentive plans

Equity incentives

Job summary

Lifted, an Upwork Company™, is seeking an experienced enterprise sales leader in the United States to build and manage a strategic pipeline for new logo acquisition. You will engage senior stakeholders across Procurement, HR, and Legal, owning the full sales cycle from prospecting to close.

The role requires 10+ years in enterprise sales, a track record of closing multi-stakeholder deals, and deep knowledge of contingent workforce models (IC, AOR, EOR, MSP, VMS).

Qualifications

• 10+ years in enterprise new business sales.
• Experience in contingent workforce, staffing, HR tech, or procurement tech.
• Proven track record of closing complex, multi-stakeholder deals (6-18+ month cycles).
• Strong understanding of contingent workforce models (IC, AOR, EOR, MSP, VMS).
• Executive presence for C-level conversations.
• High ownership and pipeline discipline.

Responsibilities

• Build and manage a targeted enterprise pipeline to drive new logo acquisition
• Lead outbound engagement with senior stakeholders in Procurement, HR, and Legal
• Own the full enterprise sales cycle from prospecting through close
• Develop deal strategy, commercial proposals, and navigate RFPs
• Partner with Solutions, Product, and Legal teams to execute deals
• Identify expansion opportunities across IC compliance, AOR, and EOR solutions

Skills

Enterprise sales

New business development

C-level engagement

Pipeline management

Negotiation

Job description

Lifted, an Upwork Company™, is seeking an experienced enterprise sales leader in the United States to build and manage a strategic pipeline for new logo acquisition. You will engage senior stakeholders across Procurement, HR, and Legal, owning the full sales cycle from prospecting to close.

The role requires 10+ years in enterprise sales, a track record of closing multi-stakeholder deals, and deep knowledge of contingent workforce models (IC, AOR, EOR, MSP, VMS).