Director, Sales

Descartes Unites the People and Technology that Move the World. The need for efficient, secure, and agile supply chains and logistics operations has become ever more critical and complex. By combining innovative technology, powerful trade intelligence and the reach of our network, Descartes helps get goods, information, transportation assets, and people where they’re needed, when they’re needed.

We’re one of the most broadly deployed logistics and supply chain technology companies in the world. More than 26,000 customers around the globe use our cloud-based solutions to transform the way they move inventory and information to enhance productivity, better serve customers, thrive competitively, keep pace with evolving regulations, and respond to rapidly changing market conditions. Descartes is publicly traded (Nasdaq:DSGX, TSX:DSG) with headquarters in Waterloo, Ontario, Canada, and offices and partners around the world. We lead the industry in innovation investment with record financial performance for more than 16 years.

Sales Director, Enterprise SaaS – North America – Global Trade

Location: Remote – United States or Canada

Compensation: $125,000–$135,000 USD Base Salary + Variable Commission

Mission

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

1. 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.

2. 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.

3. 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.

4. 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.

5. Model Consultative Selling Excellence

Partner with representatives on strategic opportunities, helping teams uncover business challenges, quantify value, and align Descartes solutions to customer outcomes.

6. 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.

7. 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.

Skills & Competencies

Leadership & Sales Excellence

• 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.

What’s In It for You

• 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.

Salary Range: $125,000 to $135,000 USD plus sales variable commission. Compensation information provided is a good faith estimate for this position only. Factors that may be used to determine your actual salary may include your specific skills as well as the years of experience you have. Similar positions located in different geographic regions will not necessarily receive the same compensation.

Location: This is a remote opportunity open to applicants authorized to work in the United States or Canada. Descartes is a global organization that uses English as a primary business language, with local language support provided where required.

#LI-Remote #Remote

Join Us

As we scale, we’re looking for new doers, collaborators and innovators to join Descartes in uniting the people and technology that move the world as the Global Leader in Logistics and Supply Chain Technology. We’re entrepreneurial, hardworking, geeky-in-a-good way problem solvers. Guided by our values, we nurture a TEAM focused culture that invests in people and creates opportunities for advancement across a broad spectrum of career paths. We prioritize work-life balance and foster an environment with the space to take ownership, to be heard, and to carve a path for your individual accomplishments to help drive our success.

Descartes also has a deep sense of environmental responsibility. Learn more about how we helped our customers save over 552,000 metric tons of CO2 in 2020 by reducing fuel and paper consumption. Join a team that’s committed to working with customers to conserve resources and enhance sustainability.

At Descartes, everyone has a voice and the best idea wins, regardless of who makes it. 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. If you feel you have 70% of the qualifications we are looking for, and Descartes sounds like the team and the mission you want to be part of, apply now. We can’t promise it will be a fit, but we do promise to consider your experience.

We conduct a mix of in-person and virtual interviews. Virtual interviews are held via Microsoft Teams and are recorded and transcribed. We may utilize AI tools to support our hiring team in notetaking, summarization, and internal training. AI tools are not used in our recruitment process for decision-making purposes. Recordings, transcripts, and notes are used for recruitment, including improvement of our process, and record-keeping purposes. Should you have any questions or concerns about our process, please connect with our hiring team in advance of scheduled interviews.

We are an Equal Employment/Affirmative Action employer. We do not discriminate in hiring on the basis of sex, gender identity, sexual orientation, race, color, religious creed, national origin, physical or mental disability, protected Veteran status, or any other characteristic protected by federal, state, or local law. For more information about our commitment to equal employment opportunity, please review our EEO is the Law, Pay Transparency Nondiscrimination Statement, EEO/AA Statement. Descartes participates in the E-Verify program. Descartes is committed to working with and providing reasonable accommodations to job applicants with disabilities. Applicants in North America with a disability who require a reasonable accommodation for any part of the application or hiring process can email us at View email address on click.appcast.io. Provide your name and contact information along with the accommodation needed to assist you with the application process. Your request will be responded to as soon as possible. Reasonable accommodations will be determined on a case-by-case basis.