Sales Director

Lifted, an Upwork Company

Sales Director responsible for landing new enterprise clients and managing full sales cycle at Lifted. Focused on contingent workforce management solution for enterprises.

Posted 7/28/2026full-timeRemote • 🇺🇸 United StatesLead💰 $151,750 - $200,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive experience in enterprise sales, particularly within contingent workforce and procurement technology, with a strong ability to manage complex sales cycles and engage with senior stakeholders. Proven track record in pipeline management, deal strategy development, and navigating compliance frameworks.

Highest-signal resume keywords

Enterprise New Business SalesContingent Workforce ModelsComplex Deal ClosingPipeline ManagementExecutive Presence

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Sales Cycle ManagementDeal Strategy DevelopmentRFP NavigationForecastingOpportunity Qualification

Soft Skills

High OwnershipStrong Follow-ThroughC-Level Engagement

Tools & Technologies

Procurement TechnologyHR TechWorkflow Automation Solutions

Industry Keywords

Contingent WorkforceStaffingAOREORMSPVMSCompliance Frameworks

About the role

Key responsibilities & impact

Build and manage a targeted enterprise pipeline to consistently drive new logo acquisition
Lead outbound engagement with senior stakeholders
Run discovery across workforce strategy, compliance, procurement, and technology
Create and advance qualified opportunities aligned to Lifted’s core offering
Own the full enterprise sales cycle through close, meeting or exceeding quota targets
Develop deal strategy, positioning, and commercial proposals
Navigate complex procurement processes, RFPs, and multi-round evaluations
Maintain disciplined pipeline management and accurate forecasting
Identify expansion opportunities across IC compliance, AOR, and EOR, staffing, and workflow automation solutions
Position Lifted within the broader contingent workforce ecosystem
Drive strategic account penetration and long-term revenue potential
Partner with Solutions, Product, Legal, and Delivery to win and execute deals successfully
Collaborate with Marketing and Sales leadership to improve pipeline development and conversion

Requirements

What you’ll need

10+ years in enterprise new business sales within contingent workforce, staffing, HR tech, or procurement tech
Proven ability to close complex, multi-stakeholder deals (6 to 18+ month cycles)
Strong understanding of contingent workforce models (IC, AOR, EOR, MSP, VMS, compliance frameworks)
Executive presence and ability to navigate C-level conversations
High ownership, strong pipeline discipline, and consistent follow-through
Comfortable operating in a fast-moving, evolving environment

Benefits

Comp & perks

comprehensive medical coverage for you and your family
unlimited PTO
a 401(k) plan with matching
12 weeks of paid parental leave