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Added 10 mins ago
M
Software Engineer II
Microsoft
Vancouver, BC
- Full-time
As a Software Engineer II on our team, you will design, develop, test, and maintain components of highly scalable and reliable cloud infrastructure. You will solve technical challenges…
Added 10 mins ago
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Cloud & AI Solution Engineer - Azure Platform
Microsoft
Toronto, ON
- Full-time
…challenges in the AI era? Join us as a Cloud & AI Solution Engineer - Azure Platform for enterprise and commercial customers at…
Added 10 mins ago
S
DCN Design for Manufacturing Engineer
SLB
Calgary, AB
- Full-time
SLB is seeking a highly motivated Design for Manufacturing (DFM) Engineer to join its Data Center business. This individual will serve as a key liaison between Product Design, Engineering,…
Added 10 mins ago
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Software Engineer, Machine Learning
Qualcomm
Markham, ON
- Full-time
…bleeding edge AI technology. In this position you will build high performance software for AI engines to extend our AI solutions into industry leading customer use cases. New…
Added 39 mins ago
BM
HVAC (heating, ventilation and air conditioning) engineer
Barrier Marine Services (Canada) Ltd
North Vancouver, BC
- Full-time
Conduct research into the feasibility, design, operation and performance of mechanisms, components and systems
Added 39 mins ago
A
Finance Solutions Engineer - EPM
Abacum
Toronto, ON
- Full-time
Abacum is the leading Business Planning solution for finance teams to drive performance. By automating reporting, enabling collaboration, and simplifying planning and forecasting, we help…
Added 39 mins ago
S
DCN Design for Manufacturing Engineer
SLB
Calgary, AB
- Full-time
SLB is seeking a highly motivated Design for Manufacturing (DFM) Engineer to join its Data Center business. This individual will serve as a key liaison between Product Design, Engineering,…
Added 55 mins ago
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Advanced Process Control Engineer
Dexcent
Fort McMurray, AB
- Full-time
Dexcent Inc. has an opportunity for a Advanced Process Control Engineer to join our growing team in Fort McMurray, AB. The individual will be required to be on site and to relocate to…
Added 55 mins ago
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Senior Site Reliability Engineer
Punt
Canada
- Full-time
We’re seeking a Senior Site Reliability Engineer to join Production Engineering, the team that help advance our infrastructure, security, reliability, and platform maturity. This is a…
Added 55 mins ago
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Frontend Software Engineer (Intermediate)
Punt
Canada
- Full-time
We are seeking an Intermediate Frontend Engineer to help build and scale the frontend for our online social gaming platform. This is a hands-on engineering role for someone with solid…
Added 55 mins ago
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Backend Engineer (Intermediate)
Punt
Canada
- Full-time
…the platform, contributing to the architecture, reliability, performance, and operational maturity of services that support a fast-growing social gaming business. We are looking for an…
Added 55 mins ago
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Senior Data Engineer (Lead)
Punt
Canada
- Full-time
We are looking for a Senior Data Engineer to join our Data Spine function. The team owns the canonical event contract, the warehouse, the certified data layer and the serving layer. Every…
Added 55 mins ago
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Site Reliability Engineer (Intermediate)
Punt
Canada
- Full-time
We’re seeking a Site Reliability Engineer to help advance our infrastructure, security, reliability, and platform maturity. This is an individual contributor role for someone who can…
Added 55 mins ago
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Senior Backend Software Engineer
Punt
Canada
- Full-time
…core of the platform, shaping the architecture, reliability, performance, and operational maturity of services that support a fast-growing social gaming business. We are looking for an…
Added 55 mins ago
P
Senior Frontend Software Engineer
Punt
Canada
- Full-time
We are seeking a Senior Frontend Engineer to help design, build, and scale the frontend architecture for our online social gaming platform. This is a hands-on engineering role for someone…
Added 55 mins ago
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Associate Data Engineer
Punt
Vancouver, BC
- Full-time
We are seeking an Associate Data Engineer to design, build, and maintain the core data pipelines and analytics models that power our platform. Working alongside senior engineers, you will…
Added 1 hour ago
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Senior Windows Server Automation Engineer
Swoon
Toronto, ON
- Contract
Senior Windows Server Automation Engineer - Contract - Hybrid, Toronto (Financial District)
Added 1 hour ago
Software Engineer - WiFi
Eagle Wireless
Richmond, BC
We are looking for a talented Software Engineer – Wi-Fi to design, develop, and maintain Linux-based embedded systems for IoT devices. This role focuses on Wi-Fi connectivity, networking…
Added 1 hour ago
TP
Senior Electrical Engineer A
Tetra Pak
Toronto, ON
- $110,800 to $158,200 CAD / year
- Full-time
…industry-leading processing solutions. The Senior Electrical Engineer will make technical decisions and be responsible for the electrical solutions and standards…
Added 1 hour ago
TP
Senior Automation Engineer A
Tetra Pak
Toronto, ON
- $110,800 to $158,200 CAD / year
- Full-time
…industry-leading processing solutions. The Senior Automation Engineer will make technical decisions and be responsible for the automation solutions and standards…
Added 1 hour ago
OT
Analyste en modélisation et simulation électrique / Electrical Modeling and Simulation Analyst
OPAL-RT TECHNOLOGIES
Montreal, QC
- Full-time
Added 1 hour ago
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Associate Cloud Engineer
''
Florenceville-Bristol, NB
- Full-time
McCain is seeking an Associate Cloud Engineer to join our Infrastructure, Engineering & Operations team. In this early-career role, you will help deploy, operate, secure, and monitor cloud…
Added 1 hour ago
S
Data & AI Solution Architect
SaskTel
Regina, SK
- Contract
…employees that promotes and supports the development of the high performance work environment critical to SaskTel's success. SaskTel’s Technical Career Path Program offers an opportunity to…
Added 1 hour ago
SE
Supplier Quality Engineer
Siemens Energy
Oakville, ON
- Full-time
Added 1 hour ago
BF
Directeur(trice), Groupe des réparations structurales / Manager, Engineering Field Repairs
Bell Flight
Mirabel, QC
- Full-time
Work with the Chief Engineer to manage the needs, performance, and individual careers of the team members.

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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