[Remote] Director, Sales

Note: The job is a remote job and is open to candidates in USA. Descartes Systems Group is a leading logistics and supply chain technology company that helps businesses improve their operations through innovative solutions. They are seeking a Sales Director for their Enterprise SaaS division to build and lead a high-performing sales team, drive revenue growth, and enhance sales effectiveness through coaching and accountability.

Responsibilities

• Develop and retain a team of 5–6 Enterprise Sales Representatives that consistently achieves or exceeds quota attainment, pipeline generation, and activity targets
• Achieve and exceed regional new business revenue targets through disciplined pipeline management, effective forecasting, and strong execution across the sales cycle
• Implement a structured coaching cadence including regular 1:1s, deal reviews, and development plans that measurably improve win rates, sales productivity, and rep performance
• Establish consistent CRM usage and data-driven sales management practices that improve forecast reliability and pipeline quality across the region
• Partner with representatives on strategic opportunities, helping teams uncover business challenges, quantify value, and align Descartes solutions to customer outcomes
• Build a strong talent pipeline, attract high-caliber sales professionals, and develop future leaders who embody Descartes’ values and sales methodology
• Create a high-performance environment where individuals take ownership of results, embrace feedback, celebrate success, and continuously raise the bar

Skills

• Proven success leading Enterprise SaaS sales teams in complex B2B environments
• Strong coaching and mentoring capabilities with a demonstrated ability to improve individual and team performance
• Deep understanding of consultative, value-based sales methodologies and enterprise buying processes
• Ability to balance strategic planning with hands-on execution in key opportunities
• Experience managing sales pipelines, forecasting, and performance metrics within CRM platforms
• Skilled in recruiting, onboarding, and developing top-performing sales talent
• Strong business acumen with the ability to connect customer challenges to measurable business outcomes
• Excellent communication, presentation, negotiation, and stakeholder management skills
• Resilient, adaptable, and comfortable leading teams through change and ambiguity
• Demonstrated ability to make data-driven decisions and hold teams accountable for results

Benefits

• Variable Commission
• Lead a critical enterprise sales region for a global SaaS company transforming logistics and supply chain performance.
• Join a culture that prioritizes coaching, leadership development, and long-term career growth.
• Gain significant visibility with senior leadership while directly influencing revenue growth and organizational success.
• Develop future sales leaders and leave a lasting impact on the performance and culture of your team.
• Operate with autonomy and ownership while receiving support from experienced leaders and cross-functional partners.
• Work remotely from anywhere in the United States or Canada with the flexibility to manage your region and team effectively.
• Access industry-leading technology, sales enablement resources, and a collaborative environment focused on continuous improvement.
• Participate in a competitive compensation program that rewards performance and results.
• We offer competitive compensation, great benefits, remote and flexible work hours, and the opportunity to join a company on an awesome mission with a great existing team and trajectory.

Company Overview