Sales Director

Accountabilities:: Enterprise Business Development: Build, develop, and manage a targeted pipeline of enterprise prospects to consistently generate new business opportunities and acquire strategic customer accounts. Full-Cycle Sales Management: Take ownership of the complete enterprise sales process, from outbound prospecting and discovery to solution positioning, commercial negotiations, and contract execution, while consistently achieving or exceeding revenue targets. Executive Engagement: Establish relationships with senior stakeholders and decision-makers across Procurement, HR, Talent Acquisition, Legal, Finance, business units, and contingent workforce management leadership. Consultative Selling: Lead discovery conversations to understand clients' workforce strategies, compliance challenges, procurement requirements, and technology needs, translating them into tailored business solutions. Solution Positioning: Present and promote a comprehensive portfolio of workforce solutions, including Independent Contractor (IC) management, Agent of Record (AOR), Employer of Record (EOR), staff augmentation, outsourced services, and workflow automation. Strategic Deal Execution: Develop effective sales strategies, prepare commercial proposals, and navigate complex procurement processes, RFPs, and multi-stage enterprise evaluations, including lengthy sales cycles. Revenue Growth and Expansion: Identify opportunities to introduce additional solutions across existing and prospective accounts, increasing strategic account penetration and long-term revenue potential. Pipeline and Forecast Management: Maintain accurate CRM records, manage sales opportunities with discipline, monitor pipeline performance, and provide reliable revenue forecasts. Cross-Functional Collaboration: Partner with Solutions, Product, Legal, and Delivery teams to develop competitive proposals, address client requirements, and ensure successful deal execution. Sales Optimization: Collaborate with Marketing and Sales leadership to strengthen prospecting strategies, improve pipeline generation, and enhance conversion rates. Requirements: Professional Experience: At least 10 years of experience in enterprise new-business sales, particularly within contingent workforce management, staffing, HR technology, or procurement technology. Industry Knowledge: Direct experience selling to enterprise workforce, talent management, and contingent workforce program leaders. Complex Sales Expertise: Demonstrated success closing high-value, multi-stakeholder enterprise deals, including sales cycles lasting approximately 6 to 18 months or longer. Contingent Workforce Expertise: Strong understanding of workforce engagement models, including Independent Contractor (IC), Agent of Record (AOR), Employer of Record (EOR), Managed Service Provider (MSP), and Vendor Management System (VMS), as well as relevant compliance frameworks. Business Development Skills: Proven ability to build a qualified enterprise pipeline from the ground up, generate new opportunities independently, and consistently deliver against ambitious sales quotas. Executive Communication: Strong executive presence and the ability to lead strategic conversations, influence C-level stakeholders, and communicate complex business solutions effectively. Commercial Acumen: Excellent negotiation, relationship-building, and deal-management skills, with the ability to develop compelling value propositions and close complex opportunities. Ownership and Accountability: Highly self-motivated, proactive, and results-oriented, with strong follow-through, forecasting discipline, and a commitment to achieving measurable outcomes. Adaptability: Comfortable working in a fast-moving, entrepreneurial environment where processes and priorities may evolve. Collaboration: Ability to work effectively across multiple departments, welcome constructive feedback, and contribute to shared business objectives. Strategic Mindset: Demonstrated curiosity, problem-solving abilities, and a continuous improvement mindset, with the confidence to challenge existing approaches and identify new opportunities. Benefits: Competitive annual base salary ranging from $151,750 to $200,000 USD, depending on qualifications, experience, skills, and geographic location. Eligibility for an annual bonus or sales incentive plan. Opportunity to participate in a long-term equity incentive program. Comprehensive medical insurance coverage for employees and their families. Unlimited paid time off (PTO). 401(k) retirement savings plan with employer matching contributions. 12 weeks of paid parental leave. Remote work environment. Professional growth and development opportunities within a rapidly expanding, technology-driven organization. Collaborative and innovative culture that encourages ownership, curiosity, accountability, and continuous learning.