Enterprise Account Executive-Transportation Management

Descartes Group; Southwestern Ontario; Remote; CAD 126,000 - 154,000; Full time

Job summary

Descartes Systems Group Inc. is seeking an Account Executive – Remote to win new enterprise customers and drive growth for Descartes’ shipping solutions.

Reporting to the Director of Sales, you will build trusted relationships with prospects, uncover business challenges, and connect needs to solutions that deliver measurable value. You will develop a robust pipeline, qualify opportunities, and progress complex deals to close, while collaborating across teams in a fast-moving remote environment.

Qualifications

• Consultative enterprise selling approach to uncover business value
• Strong ability to qualify rigorously and maintain momentum through to close
• Ability to build credibility with multiple stakeholders in large organizations

Responsibilities

• Achieve or exceed annual new-business sales targets by building a healthy pipeline of enterprise opportunities
• Develop a consistent pipeline of enterprise prospects through proactive prospecting and strategic account development
• Progress and close complex sales opportunities by identifying pain points, drivers, and measurable ROI
• Build strong relationships with key stakeholders and decision-makers to position Descartes as a trusted partner
• Demonstrate clear business value by linking Descartes capabilities to customer priorities
• Maintain disciplined pipeline and forecast management with accurate visibility into opportunities, risks, and next steps
• Collaborate across Descartes to bring the right expertise into opportunities and share market insights

Skills

Enterprise SaaS sales

Prospecting

Qualifying opportunities

Negotiation

Relationship building

Forecasting

Job description

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. With record financial performance for more than 16 years, we lead the industry in innovation investment. Every day, logistics service providers, manufacturers, retailers, distributors, and other logistics-intensive businesses of all sizes rely on our scale, stability, and comprehensive solution footprint to move what’s most important to them. Learn more at www.descartes.com. We’re growing fast and invite you to join our amazing team.

Account Executive – Remote

Reporting to theDirector of Sales, the Account Executive will be responsible for winning new enterprise customers and contributing directly to Descartes’ continued growth.

Mission

The mission of the Enterprise Account Executive is to accelerate new business growth by identifying, developing, and closing high-value enterprise opportunities for Descartes’ shipping solutions. You will build trusted relationships with prospects, uncover meaningful business challenges, and connect those needs to solutions that deliver measurable value—expanding Descartes’ market presence and creating long-term customer relationships.

Outcomes

In this role, you will:

• Achieve or exceed annual new-business sales targets by building and converting a healthy pipeline of qualified enterprise opportunities.
• Develop a consistent pipeline of enterprise prospects through proactive prospecting, strategic account development, networking, and effective qualification.
• Progress and close complex sales opportunities by identifying customer pain points, business drivers, decision criteria, compelling events, and measurable reasons to buy.
• Build strong relationships with key stakeholders and decision-makers, positioning Descartes as a trusted partner capable of solving critical logistics challenges.
• Demonstrate clear business value by connecting Descartes’ capabilities to customer priorities and articulating a compelling business case throughout the sales process.
• Maintain disciplined pipeline and forecast management, providing accurate, timely visibility into opportunities, risks, next steps, and expected results.
• Collaborate effectively across Descartes to bring the right expertise into opportunities and share customer and market insights that can inform our solutions and go-to-market strategy.

Skills & Competencies

You are a consultative enterprise seller who combines commercial drive with curiosity, discipline, and a strong focus on customer value. You are comfortable creating opportunities, navigating complex buying processes, qualifying rigorously, and maintaining momentum through to close.

You bring:

• A demonstrated track record of success in B2B SaaS or enterprise solution sales, including winning new business and closing complex opportunities.
• Strong prospecting and business-development skills, with the drive to create pipeline rather than relying solely on inbound opportunities.
• A consultative approach to selling, with the ability to uncover business challenges, ask insightful questions, and translate customer needs into measurable business value.
• Strong qualification skills and the confidence to identify where a genuine business case exists—and where it does not.
• The ability to build credibility and relationships with multiple stakeholders across an enterprise buying process.
• Strong negotiation, communication, presentation, and active-listening skills.
• Commercial judgment and the ability to manage a portfolio of opportunities while prioritizing the deals most likely to generate meaningful results.
• A disciplined, metric-driven approach to pipeline management, forecasting, and sales execution.
• The ability to collaborate effectively in a fast-moving, remote environment while taking ownership of your individual 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

Meaningful impact: Descartes doubled sales last year and plans to continue that growth trajectory. Your results will have a direct impact on new business growth, and the customer and market insights you bring back to the organization can help shape how our solutions evolve.

Ownership and visibility: You will own enterprise opportunities from prospecting and qualification through negotiation and close, with visibility to sales leadership and opportunities to collaborate across the business.

Growth opportunities: As Descartes grows, you will have opportunities to deepen your enterprise sales expertise, expand your scope, and take on increasingly complex and strategic opportunities.

Collaborative, high-energy environment: You will join a growing remote sales team where you will have autonomy to manage your territory and opportunities while collaborating with colleagues and subject‑matter experts to win business.

Market-leading solutions: You will represent an established organization and bring Descartes’ logistics solutions to enterprise customers facing meaningful and complex business challenges.

Location and Compensation

This is a remote opportunity open to applicants authorized to work in the United States.

The base salary range for this position is $90,000 to 110,000 USD, plus uncapped sales commission, with expected On-Target Earnings (OTE) of $170,000–$190,000 USD.

Compensation information provided is a good-faith estimate for this position only. Factors used to determine actual salary may include specific skills and years of relevant experience. Similar positions located in different geographic regions will not necessarily receive the same compensation.

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, we can't promise it will be a fit, but we do promise to consider your experience.

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 [e-mail]. 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.

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.

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: https://www.descartes.com/who-we-are/social-responsibility-sustainability/environmental-impact. Join a team that’s committed to working with customers to conserve resources and enhance sustainability.