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Canada
Remote only
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Sales Director based in Canada.
We are looking for an accomplished Sales Director to drive enterprise new business acquisition and generate significant revenue growth in the global contingent workforce management market.
In this senior, quota-carrying role, you will own the entire enterprise sales cycle, from prospecting and pipeline development to negotiation and closing high-value deals.
You will engage with senior decision-makers across Procurement, HR, Talent Acquisition, Legal, Finance, and business leadership.
You will position a comprehensive portfolio of workforce solutions, including Independent Contractor (IC), Agent of Record (AOR), Employer of Record (EOR), staff augmentation, and outsourced services.
Working in a fast-paced, evolving environment, you will help enterprises simplify workforce management, improve compliance, and gain greater operational visibility.
This is an opportunity for a commercially driven leader who enjoys building pipelines from scratch, navigating complex sales processes, and shaping the future of work.
As Sales Director, you will lead enterprise business development initiatives, manage complex commercial opportunities, and consistently deliver new revenue. Your main responsibilities will include:
New Logo Acquisition:
Build, develop, and manage a targeted enterprise sales pipeline to consistently acquire new customers.
Lead proactive outbound engagement with senior executives and key enterprise stakeholders.
Conduct discovery sessions covering workforce strategy, compliance, procurement requirements, and technology needs.
Identify, qualify, and advance opportunities aligned with the organization's core solutions.
Develop strategic relationships with enterprise workforce, talent, and contingent workforce leaders.
Enterprise Deal Ownership:
Own the complete enterprise sales cycle, from initial prospecting through negotiation and contract execution.
Consistently meet or exceed assigned sales quotas and revenue targets.
Develop compelling deal strategies, value propositions, positioning, and commercial proposals.
Navigate complex procurement processes, requests for proposals (RFPs), and multi-stage evaluation procedures.
Maintain accurate pipeline records, disciplined opportunity management, and reliable revenue forecasts.
Manage long sales cycles involving multiple stakeholders and competing business priorities.
Strategic Positioning & Revenue Growth:
Identify opportunities to expand enterprise relationships across IC compliance, AOR, EOR, staffing, and workflow automation solutions.
Position the full portfolio within the broader contingent workforce management ecosystem.
Identify strategic account penetration opportunities and develop long-term revenue potential.
Communicate the business value of integrated workforce solutions to executive-level decision-makers.
Internal Collaboration:
Partner with Solutions, Product, Legal, and Delivery teams to develop proposals and successfully execute enterprise deals.
Collaborate with Marketing and Sales leadership to strengthen pipeline generation and improve conversion rates.
Contribute market insights and customer feedback to support continuous improvements in sales strategy and positioning.
Requirements:
The ideal candidate is a highly experienced enterprise sales professional with a proven track record of acquiring new customers and closing complex, high-value deals. You should demonstrate the following qualifications and capabilities:
10+ years of experience in enterprise new business sales, particularly within contingent workforce management, staffing, HR technology, or procurement technology.
Direct experience selling to enterprise workforce, talent management, and contingent workforce program leaders.
Proven ability to successfully close complex, multi-stakeholder enterprise deals with sales cycles typically ranging from 6 to 18+ months.
Strong understanding of contingent workforce models and solutions, including Independent Contractor (IC), Agent of Record (AOR), Employer of Record (EOR), Managed Service Provider (MSP), and Vendor Management System (VMS).
Knowledge of workforce compliance frameworks and the challenges associated with managing global contingent talent.
Demonstrated ability to build and manage enterprise pipelines independently, particularly through proactive outbound prospecting.
Strong executive presence and confidence navigating C-level discussions and strategic negotiations.
Excellent commercial judgment, deal structuring, and consultative selling skills.
High level of ownership, accountability, pipeline discipline, and consistent follow-through.
Ability to operate effectively in fast-moving, evolving, and entrepreneurial environments where processes may still be developing.
Strong collaboration skills and the ability to influence cross-functional teams.
Comfortable working toward ambitious targets and adapting to constructive feedback and changing priorities.
Benefits:
Annual base salary ranging from $151,750 to $200,000 USD, depending on experience, qualifications, skills, and location.
Eligibility for an annual bonus or sales incentive plan.
Eligibility to participate in a long-term equity incentive program.
Comprehensive medical coverage for employees and their families.
Unlimited paid time off (PTO).
401(k) retirement plan with employer matching.
12 weeks of paid parental leave.
Opportunities for professional development, continuous learning, and career growth.
Opportunity to work in a dynamic, fast-growing environment combining startup agility with global enterprise impact.
Inclusive and collaborative culture built around trust, innovation, curiosity, excellence, and ownership.
Opportunity to influence the future of global workforce management and enterprise talent solutions.