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Administrative Assistant, Senior
Bombardier
Dorval, QC
- Full-time
Minimum of seven (7) years of experience in a similar coordination or senior technical support role.
Added 2 mins ago
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Lead, FP&A Manager
OpenText
Mississauga, ON
- Full-time
…executive presentations, business cases, and recommendations for senior…
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Sr. FP&A Manager
OpenText
Mississauga, ON
- Full-time
…executive presentations, business cases, and recommendations for senior…
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Director, Product - Insurance
GreenShield
Toronto, ON
- Full-time
Comfortable working with all levels of the organization – especially senior executives.
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Professional Senior Engineering, Stress Integration
Bombardier
Montreal, QC
- Full-time
Job Professional Senior Engineering, Stress Integration
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OE
Production Test Tech (2nd Shift)
OSI Electronics
Toronto, ON · Scarborough, ON
- $18 CAD / hour
- Full-time
It is the responsibility of every employee to report to their manager or a member of senior management any quality problems or defects in order for corrective action to be implemented and…
Added 2 mins ago
OE
General Labourer - Floater (2nd Shift)
OSI Electronics
Toronto, ON · Scarborough, ON
- $18 CAD / hour
- Full-time
It is the responsibility of every employee to report to their manager or a member of senior management any quality problems or defects in order for corrective action to be implemented and…
Added 2 mins ago
OE
General Labourer - Floater
OSI Electronics
Toronto, ON · Scarborough, ON
- $18 CAD / hour
- Full-time
It is the responsibility of every employee to report to their manager or a member of senior management any quality problems or defects in order for corrective action to be implemented and…
Added 2 mins ago
Senior Manager, Account Management - Questbank
Questrade Financial Group
Toronto, ON
We’re looking for our next Senior Manager, Account Management. Could It Be You?
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AI Product Engineer
Angel Host
Montreal, QC
- Full-time
You reduce the volume of work that reaches senior engineering by triaging, reproducing, and resolving issues independently
Added 17 mins ago
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Senior Cost Analyst
Worley
Markham, ON
- Full-time
This is not a traditional software developer position. It is a specialized Project Controls role with significant Power BI development responsibilities, requiring both strong analytical and…
Added 32 mins ago
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Supervisor, Bekaadendang Program (Anti-Human Trafficking/PAR/CARE TEAM)
Native Child and Family Services of Toronto
Toronto, ON
- $88,193 to $106,569 CAD / year
- Full-time
Works with senior leadership, especially the Manager of Wholistic Services, to support with hiring, determining work priorities, assigning duties, providing direction and training, setting…
Added 32 mins ago
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Talent Partner (6-month Contract)
Nelson
Toronto, ON
- Temporary
Reporting to the Senior Talent Partner, the Talent Partner will manage full-cycle recruitment, focusing on technology, product, digital, publishing, and content roles that support Nelson's…
Added 32 mins ago
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AI Product Engineer IT - Montréal, Quebec (Hybrid)
Angel Host
Montreal, QC
- Full-time
You reduce the volume of work that reaches senior engineering by triaging, reproducing, and resolving issues independently
Added 32 mins ago
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Operations Support Specialist
Hirematic Talent Solutions
Toronto, ON
- $40 to $45 CAD / hour
- Full-time
Systems Administrator / Operations Support Specialist Senior
Added 32 mins ago
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Talent Partner (6-month Contract)
Nelson Education LTD
Remote, Canada
- From $70,000 CAD / year
- Temporary
- Remote
Reporting to the Senior Talent Partner, the Talent Partner will manage full-cycle recruitment, focusing on technology, product, digital, publishing, and content roles that support Nelson’s…
Added 32 mins ago
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Specialist I, IT Enterprise GIS Technical Specialist
Enbridge
Calgary, AB · Edmonton, AB · Toronto, ON · North York
- Full-time
…Enterprise GIS Technical Specialist to join our team and provide senior technical leadership for our enterprise GIS platforms and solutions. In this role, you will be responsible for the…
Added 1 hour ago
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Indigenous Cultural Safety, Diversity, Equity and Inclusion Advisor
Workers' Safety & Compensation Commission of the NWT & Nunavut
AB · Alberta, Canada
- $106,158 to $126,809 CAD / year
- Full-time
Recommending improvements, developing action plans and measuring progress with units and senior leadership
Added 1 hour ago
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Senior Mechanical Designer
Worley
Calgary, AB · Edmonton, AB
- Full-time
Worley is seeking a Senior HVAC Designer who will work on the design of mechanical building services. The successful candidate should have the capability to work in a fast-paced…
Added 1 hour ago
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Indigenous Cultural Safety, Diversity, Equity and Inclusion Advisor
Workers' Safety & Compensation Commission of the NWT & Nunavut
Yellowknife, NT
- $106,158 to $126,809 CAD / year
- Full-time
Recommending improvements, developing action plans and measuring progress with units and senior leadership
Added 1 hour ago
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RQ11717 – Business Analyst – Senior
S M Software Solutions Inc
Toronto, ON
- Internship
We are seeking a highly experienced Senior Business Analyst with over 10 years of experience in business analysis, requirements gathering, business process re-engineering, business case…
Added 1 hour ago
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Senior Financial Analyst
DCM
Brampton, ON
- $80,133 to $100,166 CAD / year
- Full-time
As a Senior Financial Analyst, you will be the primary finance business partner for the Brampton facility, providing timely financial insight, analysis, and decision support to plant…
Added 1 hour ago
SM
RQ00245 – Machine Learning Engineer – Senior
S M Software Solutions Inc
Toronto, ON
- Full-time
We are seeking a highly skilled Senior Machine Learning Engineer with advanced hands-on experience in Azure Machine Learning, Microsoft Foundry/Azure AI Foundry, Machine Learning Operations…
Added 1 hour ago
DI
Senior Vue.js Developer - HYBRID (1900) 105-115K
Direct IT Recruiting Inc.
Toronto, ON
- $105,000 to $115,000 CAD / year
- Full-time
Seeking a Senior Vue.js front-end developer able to succeed in a stimulating and ever-changing environment, to develop and test, with creativity and innovation, critical solutions to…
Added 1 hour ago
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Senior QA and Automation Developer
Taiv
Remote, Canada
- Full-time
- Remote
We are looking for a Senior QA and Automation Developer to join our growing team!

Swoon

Senior Windows Server Automation Engineer

Toronto, ON, Canada

Compensation: $120,000–$130,000 annually, commensurate with experience. · Contract

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Job details

Pay: Compensation: $120,000–$130,000 annually, commensurate with experience.
Job type: Contract
Apply by: Nov 28, 2026
Posting language: English
Posted: Oct 29, 2026

Original job description

Senior Windows Server Automation Engineer - Contract - Hybrid, Toronto (Financial District)

Our client - one of Canada’s Big 5 banks - is hiring a Senior Windows Server Automation Engineer for their Windows Engineering team. This is a hands-on, automation-first role: you’ll spend your time designing and building reusable, production-grade automation, not chasing tickets. If you write Ansible and/or Python like a developer - modular, idempotent, source-controlled, tested - and you know Windows Server infrastructure cold, this is built for you.

What you’ll do

Design, develop, and maintain reusable, production-grade automation using Ansible and/or Python for end-to-end server lifecycle: OS deployment across physical and virtual environments, configuration, domain integration, security hardening, compliance validation, and patch readiness.
Apply real software-engineering practice - source control, modular/idempotent design, testing, logging, error handling, secrets management, code review, and CI/CD. PowerShell where it makes sense for Windows integration.
Design, automate, and troubleshoot enterprise Group Policy and Windows Server security baselines across a large estate, with targeted rollout, drift detection, and remediation.
Lead performance analysis, complex troubleshooting, and root-cause resolution across OS, virtualization, storage, networking, identity, and security.
Own technical designs and production outcomes, review code, and work across infrastructure, security, and operations teams.

What you bring

8+ years engineering and supporting large, complex enterprise Windows Server environments (physical, virtual, hybrid).
Substantial, hands-on experience independently building and maintaining reusable automation in Ansible and/or Python - frameworks, roles, playbooks, modules, or tooling - with strong engineering discipline (source control, testing, CI/CD).
Advanced Group Policy and Active Directory depth (OUs, inheritance/precedence, WMI and security filtering, delegation, conflict resolution) plus hands-on security-baseline design and automation.
Core Windows infrastructure strength: failover clustering, Kerberos, certificates, patching, and vulnerability remediation.
Working networking knowledge (TCP/IP, DNS, DHCP, subnetting, routing, load balancers) and performance tuning with tools like PerfMon and WPR/WPA.

Nice to have

Microsoft, Red Hat Ansible, or Python certification.
VMware/Hyper-V, cloud, and regulated-enterprise (financial services) experience.

Hybrid role (2-3 days/week onsite) based in downtown Toronto (Financial District). Contract. Compensation: $120,000–$130,000 annually, commensurate with experience.

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More about this job

Responsibilities

Design, build, and maintain reusable, production-grade automation for Windows Server deployment, configuration, security hardening, compliance, and patch readiness. Lead Group Policy and security-baseline automation, complex infrastructure troubleshooting, technical design, code reviews, and collaboration across infrastructure, security, and operations teams.

Requirements

Requires 8+ years supporting large enterprise Windows Server environments and substantial hands-on experience building reusable Ansible and/or Python automation using disciplined software-engineering practices. Candidates should have advanced Group Policy and Active Directory expertise, Windows security-baseline experience, strong core Windows infrastructure knowledge, and working networking and performance-tuning skills.

Skills

Windows Server
Ansible
Python
PowerShell
Automation
Group Policy
Active Directory
Security Baselines
Failover Clustering
Kerberos
Certificates
Patch Management
Vulnerability Remediation
TCP/IP Networking
Performance Tuning
CI/CD

Visa sponsorship

Not detected in the job text

Keywords

Windows Server
Ansible
Python
PowerShell
Server Lifecycle Automation
Physical Servers
Virtualization
Active Directory
Group Policy
Security Baselines
Security Hardening
Compliance Validation
Patch Readiness
Source Control
Idempotent Design
Testing
Logging
Secrets Management
Code Review
CI/CD
Failover Clustering
Kerberos
Certificates
Vulnerability Remediation
TCP/IP
DNS
DHCP
PerfMon
WPR/WPA
Financial Services

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