[Hiring] Sales Director, Enterprise SaaS @The Descartes

Role Description

At Descartes, we believe great sales organizations are built through coaching, accountability, and customer-focused leadership. As a Sales Director, Enterprise SaaS, your mission is to develop high-performing sales professionals who consistently create value for customers, accelerate new business growth, and build lasting competitive advantage across North America. You will serve as a player-coach, helping your team win complex enterprise opportunities while developing future sales leaders through intentional coaching, disciplined execution, and a culture of continuous improvement.

Outcomes

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

Qualifications

• 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.

Culture Add: TEAM Values

• We value team members who communicate with transparency, sharing information openly and building trust across functions.
• You bring excellence and expertise to your craft, holding a high bar for quality while continuously improving your skills.
• You demonstrate accountability by owning outcomes, following through on commitments, and taking responsibility for results.
• You are driven by metrics, using data and experimentation to inform decisions and deliver measurable impact.

Aptitudes

• Smart: Able to quickly understand complex systems, connect ideas, and make sound judgments.
• Curious: Actively seeks to understand customer problems, emerging technologies, and better ways of working.
• Coachable: Open to feedback, willing to adapt, and continuously improving through learning.

Benefits

• 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.