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Title:  Senior MS Systems Administrator/AD Specialist


Waterloo, ON, CA, N2V 1C6

About Descartes: 

Descartes (TSX:DSG) (Nasdaq:DSGX) is the global leader in providing on-demand, software-as-a-service solutions focused on improving the productivity, performance and security of logistics-intensive businesses. Descartes has over 147,000 parties using its cloud based services. Customers use our modular, software-as-a-service solutions to route, schedule, track and measure delivery resources; plan, allocate and execute shipments; rate, audit and pay transportation invoices; file customs and security documents for imports and exports; and complete numerous other logistics processes by participating in the world's largest, collaborative multimodal logistics community. Our headquarters are in Waterloo, Ontario, Canada and we have offices and partners around the world. Learn more at

We are currently seeking a Senior Microsoft Systems Administrator to join our Implementations and Maintenance Services (IMS) Team. As a member of the team, you will be responsible for designing and implementing changes, upgrades, and projects required to maintain our infrastructure to support business needs.  This includes managing projects from start to finish, meeting deadlines, provisioning of documentation, cross-training other team members, and creating and maintaining a knowledge base.  As a senior member of the team, you will also provide leadership and guidance to help resolve any technical challenges that may come up.  You will be required to work closely and collaborate with other IT teams and Service Delivery departments.


•    Manage infrastructure projects from start to finish and ensure commitments are delivered on time.
•    Provide leadership and guidance to help resolve technical challenges.
•    Implement and maintain on premise and cloud infrastructure on a 24x7x365 basis and respond to incidents in a timely manner.
•    Align new acquisitions and system deployments with Standard Operating Procedures and integrate IT Systems.
•    Create technical documentation and procedures related to assigned tasks or projects.
•    Incremental automation to streamline standard operating procedures.
•    Interface with development and other teams to communicate issues and recommend improvements in their respective applications.
•    Create and maintain a knowledge base for the team and assist in cross-training other team members.
•    Act as a subject-matter-expert for technical support and perform on-call duties on a rotational basis.
•    Plan and carry out after-hours changes to meet business and operational needs.


Experience and Skills Required:
•    Expert knowledge of Microsoft Windows Server, Active Directory, DHCP, DNS, Office 365, SharePoint, Group Policies, Microsoft System Center, WSUS, Orchestrator, DFS Services, VMWare, and Citrix.
•    Familiar with Identity and Access Management, Least Privilege, PAW (Privilege Access Workstation), PIM (Privilege Identity Management), PAM (Privilege Access Management)
•    Familiar with Active Directory Red Forest Model, Enhanced Security Administrative Environment (ESAE), Microsoft “Active Directory Administrative Tier Model
•    Familiar with Microsoft Domain design and domain segmentation, trusts, splitting and merging domains 
•    Familiar with Hybrid Identity (On-prem replicated to AzureAD)
•    Familiar with Entitlement Management/Azure AD Entitlement Management
•    Experience with SQL Server, SQL queries, SSIS, and SSRS.
•    Experience deploying and administering compute resources in Azure, AWS, Google or other cloud service providers.
•    Strong knowledge of Microsoft System Center Operations Manager (SCOM) from an architectural and support perspective.
•    Experience with implementing and supporting client-server applications.
•    Experience with PowerShell and Service Management Automation or similar frameworks.
•    Proven problem solving skills, service oriented, and solution driven.
•    Experience with conducting Root Cause Analysis on major incidents, coordinating and executing follow-up actions.
•    Experience with incident, change and problem management procedures in an ITIL driven environment.


Desired Attributes:
•    Ability to work and collaborate with colleagues in other offices and in different time zones.
•    Process driven and must possess excellent project/task management skills.
•    Strong drive to understand and learn on the job.
•    Ability to work independently without direct supervision on internal projects, functional testing and analysis of requirements for new and existing services.
•    Ability to effectively handle multiple concurrent projects and prioritize based on business and operational needs.
•    Excellent and proven communication (verbal and written) and consensus building skills.
•    Security awareness.
•    Highly motivated and proactive with the ability to learn and adapt quickly to changing priorities and demands.
•    Ability to perform under tight timelines in a fast-paced environment with minimal supervision.
•    Must be detail-oriented with above average organization, planning and administrative skills.
•    Responsible and accountable.


Qualifications and Certifications:
•    Must be a very strong team player with 10+ years of related work experience.
•    University Degree is preferred.  Certification(s) such as MCITP, MCSE or other Microsoft certifications are highly desirable.


We would love for you to join our offices in Waterloo (when we reopen post COVID).



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. Please click below to learn more about the E-Verify program. Notice of E-Verify Participation Right to Work (English and Spanish)

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 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.


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