Osler, Hoskin & Harcourt LLP is one of Canada’s leading business law firms. Advising many of Canada’s corporate leaders, as well as U.S. and international parties with extensive interest in Canada, our more than 1,000 firm members are based in offices in Toronto, Montréal, Ottawa, Vancouver, Calgary and New York.

Osler prides itself on attracting and maintaining some of the brightest talent in the legal arena. Our lawyers, students, management and staff have created a unique firm culture which nurtures mentoring and the exchange of ideas. Osler is a dynamic and exciting place to further your career or carve out a new path.

We are seeking a Desktop Applications Support Specialist to join our team. In this capacity, you will support the full application lifecycle which requires strong problem‑solving ability and independence. The specialist will play a crucial role in supporting Firm applications and associated services through expert understanding of software application support, system administration, service delivery, and modern cloud‑aligned desktop management within the M365 ecosystem.

This job posting is for an existing vacancy.

Major Responsibilities:

• Build & deploy Application Packages and Task Sequences to manage distribution of the Windows 11 Image, including Group Policy Object (GPO) management and equivalent/modern policy management using Microsoft Intune, applying configuration profiles, compliance policies, and security baselines
• Develop the plan and coordinate effort for installing/upgrading applications in collaboration with internal IS resources & business stakeholders.
• Provide support for Microsoft Endpoint Configuration Manager and Intune, integrating both as part of the organization’s modern management strategy
• Maintain and support Osler’s applications; act as an escalation point for first line technical teams
• Work with Windows 11 operating system configurations, ensuring optimized performance and adherence to firm standards through scripting
• While working autonomously on scripting projects, you will collaborate with the broader IT team as needed to understand requirements, test solutions, and deploy changes
• Participate actively in change control processes, including drafting change documentation, assessing risk/impact, and presenting changes for approval
• Work with cloud‑connected Windows 11 configurations, Autopilot, Azure AD device join, conditional access, Defender for Endpoint, and enterprise application integration within M365
• Participate in application lifecycle management, including vendor management, contract awareness, advising on end‑of‑life timelines, coordinating upgrades, and ensuring security and compliance requirements
• Performs all other duties as assigned

Position Requirements

Education and Experience

University degree in Computing, Computer Science, Software Engineering or Mathematics. Minimum of 5 years of experience working in a technical systems or application administrator role. An equivalent combination of education and experience may be acceptable.

Knowledge and Skills:

• Strong working knowledge of Microsoft 365 applications and integrations; working knowledge of legal technology and services is considered an asset
• Experience with GPO and modern Intune configuration (settings catalog, configuration profiles, administrative templates)
• Strong understanding of Windows operating system architecture, deployment, and management
• Strong understanding of cloud‑based identity, Azure AD, Autopilot, and device compliance
• Experience managing Windows devices using MECM/SCCM and Intune
• Exposure to or experience with Microsoft Intune and modern device management concepts
• 3+ years of advanced PowerShell scripting
• Exceptional analytical and problem‑solving abilities
• Demonstrated ability to work independently, manage time effectively, prioritize tasks, and take initiative to drive projects to completion.
• Strong verbal and written communication skills to articulate technical concepts and document solutions clearly
• Strong analysis and customer service skills with sound problem solving, judgment and decision-making skills
• Excellent documentation and communication skills
• Ability to multi-task and set priorities

We are currently working in a hybrid work arrangement, which includes a requirement to work primarily in the office and flexibility to work remotely up to 2 days per week.

Compensation:

The range of expected compensation for this position is $95,000 - $110,000 annually. Compensation offered will be based on a variety of factors including job-related knowledge, education, skills and experience.

Accessibility and Accommodation

We thank all applicants for their interest in Osler; however, only chosen applicants will be contacted. Osler is committed to fostering a diverse and inclusive work environment, and we welcome and encourage applications from people with disabilities and people with diverse backgrounds, identities, and cultures. Accommodations are available upon request for candidates in all phases of the selection process.

Background and Reference Checks

Please note that any offer of employment will be conditional upon background and reference checks, including a criminal record check, credit check, and employment and educational verifications.

If you have the required background with the ability to provide exceptional customer service and wish to work in one of Canada's leading law firms, please reply in confidence with a cover letter and résumé by the closing date.

Please note that we use artificial intelligence to screen, assess or select applicants for the position.

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