Senior Technical Support Representative

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

We’re growing fast and invite you to join our amazing team.

Mission - Why This Role Exists

As a Technical Support Analyst, you will play a key role in ensuring customers receive reliable, high-quality support for business-critical transport management software used across the world. This role exists to provide strong technical ownership of complex issues, strengthen the capability of the Support team, and help customers, colleagues, and third parties reach clear and effective solutions.

You will take a hands-on approach to investigation rather than simply passing issues on. You will form a view on root cause, guide resolution, mentor colleagues, and help shape the Support function of the future through smarter processes, AI tools, and automation.

Outcomes - What Success Looks Like

1. Own complex customer issues from start to finish, acting as a trusted escalation point and driving issues through to clear resolution.

2. Investigate and resolve data, integration, and system-related problems using structured troubleshooting, SQL, and log analysis where appropriate.

3. Provide clear technical guidance to customers, internal teams, and third parties by explaining the cause of issues, recommended fixes, and next steps.

4. Strengthen team capability by mentoring colleagues and sharing knowledge through documentation, training, and day-to-day coaching.

5. Contribute to building a strong Support team by participating in technical interviews for Support candidates.

6. Represent Support effectively in collaboration with customers, Professional Services, and Development teams.

7. Manage the handover of new customers from projects into Support, helping ensure a smooth and well-coordinated transition.

8. Identify practical opportunities to improve the Support function, including work that can transition into Support and opportunities to use AI and automation.

Skills & Competencies - How the Work Gets Done

Technical Expertise - Highly appreciated when you bring:

· Several years of experience in technical or application support for complex business software, or strong experience in transport management and logistics; ideally both

· A demonstrated ability to work independently and take full ownership of technical issues through to resolution

· Strong analytical skills and a structured, methodical approach to troubleshooting

· Clear and confident communication in English with customers, colleagues, and third parties

· Experience coaching, mentoring, or training others

Nice to Have

· Experience supporting Transport Management Systems (TMS)

· SQL skills for troubleshooting, data investigation, and analysis

· Knowledge of EDI and integrations, including EDIFACT, XML, X12, and APIs

· Interest in AI tools, automation, and new ways of improving technical support

Key Attributes

· Mature, independent, and confident in making decisions and taking ownership

· Reflective and willing to learn from setbacks, with the ability to identify what could be done differently next time

· Patient and helpful when mentoring others, while remaining direct and clear in communication

· Curious about new technology and new ways of working

· Comfortable operating with autonomy and contributing ideas that improve team effectiveness

Culture Add: TEAM Values

We value team members who communicate openly, share information transparently, and build trust across functions. You bring excellence and expertise to your craft, maintaining a high standard of quality while continuously developing your skills. You demonstrate accountability by owning outcomes, following through on commitments, and taking responsibility for results. You are driven by evidence and practical insight, using data and thoughtful experimentation to improve customer and team outcomes.

Aptitudes

· Smart: Able to quickly understand complex systems, analyse technical problems, connect information, and make sound judgments.

· Curious: Actively seeks to understand customer problems, new technologies, AI tools, and better ways of working.

· Coachable: Open to feedback, reflective about setbacks, willing to adapt, and committed to continuous improvement.

What's in It for You

· A role with real autonomy, influence, and room to grow

· A collaborative international team and a supportive culture

· The opportunity to help shape how Support uses AI and automation

· Exposure to transport, logistics, EDI, integrations, and business-critical customer processes

· Opportunities to grow within an international software company

· Fully remote working arrangement with opportunities for long-term career growth within a global software organisation.

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. 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.

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.

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 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 status, or any other characteristic protected by federal, provincial, or local law. For more information about our commitment to equal employment opportunity, please review our Code of Business Conduct and Ethics at