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Remote Level 2 It Support Jobs in Waterloo, ON (NOW HIRING)

As a Support Analyst, you'll investigate complex application issues, collaborate with teammates ... new technologies and adapting to new ways of working. * Can analyze information from multiple ...

Director, Support

Waterloo, ON ยท On-site +1

CA$85K - CA$104K/yr

... of the week can be remote or from the office based on task requirements or personal work ... Diploma or degree in Computer Science, Information Technology, Software Engineering, or a related ...

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Remote Level 2 It Support information

What is a remote level 2 IT support?

Remote Level 2 IT Support professionals provide technical assistance to users by resolving more complex IT issues that cannot be solved by Level 1 support. They work remotely to troubleshoot software, hardware, and network problems, often using remote access tools and advanced diagnostic methods. These specialists may also escalate unresolved issues to higher-level engineers, maintain documentation, and contribute to system improvements. Strong communication skills and in-depth technical knowledge are essential for this role.

What skills and qualifications are needed for remote level 2 IT support?

To excel as a Remote Level 2 IT Support specialist, you need advanced troubleshooting skills, strong knowledge of operating systems and networks, and usually a relevant IT degree or certifications like CompTIA A+ or Microsoft Certified: Windows Support. Familiarity with remote desktop tools, ticketing systems, and diagnostic utilities is essential for resolving complex user issues. Outstanding communication, patience, and problem-solving abilities help build trust and efficiently assist users remotely. These competencies ensure timely resolution of technical problems, minimize downtime, and maintain high levels of user satisfaction in a distributed work environment.

What challenges do remote level 2 IT support professionals face and how can they address them?

Remote Level 2 IT Support professionals often encounter challenges such as troubleshooting complex technical issues without physical access to devices, managing multiple support tickets simultaneously, and communicating clearly with end-users who may have varying levels of technical knowledge. To address these challenges, it's important to leverage remote diagnostic tools, maintain organized ticket management, and develop strong communication skills to guide users through solutions. Regular collaboration with Level 1 and Level 3 support teams also helps ensure escalated issues are resolved efficiently and knowledge is shared across the team.

What is the difference between Remote Level 2 It Support vs Remote Help Desk Technician?

AspectRemote Level 2 It SupportRemote Help Desk Technician
CertificationsCompTIA A+, Network+; Microsoft CertifiedCompTIA A+; Basic certifications
Work EnvironmentTechnical support, troubleshooting complex issuesCustomer support, basic troubleshooting
Employer UsageIT departments, managed service providersHelp desk services, IT support companies
Search IntentTechnical problem-solving, advanced supportBasic support, customer service

Remote Level 2 It Support involves handling more complex technical issues, requiring advanced certifications and troubleshooting skills. In contrast, Remote Help Desk Technicians focus on basic customer support and initial troubleshooting. Both roles are essential in IT support but differ in complexity and responsibilities.

What are popular job titles related to Remote Level 2 It Support jobs in Waterloo, ON?

For Remote Level 2 It Support jobs in Waterloo, ON, the most frequently searched job titles are:

What job categories do people searching Remote Level 2 It Support jobs in Waterloo, ON look for?

The top searched job categories for Remote Level 2 It Support jobs in Waterloo, ON are:

Infographic showing various Remote Level 2 It Support job openings in Waterloo, ON as of August 2026, with employment types broken down into 45% Full Time, 30% Part Time, 2% Temporary, 21% Contract, and 2% Nights. Highlights an 100% Remote job distribution.

Technical Support Representative

The Descartes Systems Group, Inc.

Waterloo, ON โ€ข Remote

CA$80K - CA$85K/yr

Full-time

Posted 5 days ago


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. ย 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.ย 


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

Mission

As a Technical Customer Support Specialist, your mission is to help enterprise customers get the most from our Transportation Management Software (TMS) by diagnosing and resolving complex technical issues.ย  You'll work directly with customers and partner with Product, Engineering, and Hosting teams to deliver timely resolutions and a strong customer experience.

Outcomes

  • Diagnose and resolve complex customer issues across our cloud-based TMS platform.
  • Own customer cases through resolution, providing clear and timely communication.
  • Partner with Product, Engineering, and Hosting teams to escalate issues and identify root causes.
  • Document solutions and contribute to a scalable technical knowledge base.
  • Develop deep product expertise and stay current on releases and platform changes.
  • Support urgent customer issues outside regular business hours when required.

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Skills & Competencies

  • 3-5 years of customer-facing software support or troubleshooting experience in a Cloud/SaaS environment, or a relevant degree in IT, Engineering, Logistics, or a related field.
  • Strong analytical, troubleshooting, and problem-solving skills.
  • Excellent written and verbal communication skills.
  • Ability to learn complex technologies quickly and work independently.
  • Knowledge of transportation modes such as TL, LTL, Parcel, and Intermodal is preferred.
  • Experience with TMS platforms, SQL, Java, JSON, or XML is an asset.

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Culture Add: TEAM Values

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

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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.

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What's in It for You

You'll build expertise at the intersection of SaaS, transportation, and supply chain technology while working directly with enterprise customers and collaborating with Product and Engineering.ย  You'll have the autonomy to solve challenging problems, influence improvements to the customer experience, and expand your technical scope as you grow.

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Location: This is a remote opportunity open to candidates authorized to work in Canada or the United States.ย  Employment sponsorship is not available for this position.

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Salary Range: $80,000 to $85,000 CAD.ย  Compensation information provided is a good faith estimate for this position only.ย  Factors that may be used to determine your actual salary may include your specific skills as well as the years of experience you have.ย  Similar positions located in different geographic regions will not necessarily receive the same compensation. #LI-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. 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.ย 

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.ย Join a team that's committed to working with customers to conserve resources and enhance sustainability.ย 

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.ย 

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.ย 

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 atย Descartes.com