Senior Windows Server Application Support Analyst (PowerShell, SQL Server,

Senior Windows Server Application Support Analyst (PowerShell, SQL Server, AutoSys)

Location: Hybrid – 4 days/week onsite, Downtown Toronto
Experience: 4+ years (Canadian enterprise experience preferred)

We're looking for a Senior Windows Server Application Support Analyst to join a high-performing IT Operations team supporting mission-critical enterprise applications in the Wealth Management / Financial Services / FinTech sector.

If you're passionate about Windows Server Administration, Application Support, PowerShell automation, SQL Server, AutoSys, and enterprise infrastructure, this is an opportunity to work on business-critical systems in a collaborative, fast-paced environment.
What You'll Do

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Install, configure, upgrade, and support Windows Server-based applications.

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Monitor and maintain production applications, Windows Services, and server resources.

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Create and support secure SFTP integrations and file transfer automation.

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Develop and maintain PowerShell Batch and or Python scripts to automate operational processes.

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Configure and manage AutoSys batch jobs and enterprise scheduling.

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Deploy and support enterprise applications alongside Development teams.

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Support SQL Server environments, perform SQL queries, and troubleshoot production issues.

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Coordinate with Infrastructure and Information Security teams to ensure compliance and server health.

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Manage SSL/TLS certificates and application security requirements.

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Provide Level 2 production support and participate in an on-call rotation.

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Document operational procedures and system configurations.

What You'll Bring

4+ years supporting Windows Server applications in an enterprise environment

Strong Windows Server Administration and Application Support experience

Hands-on experience with PowerShell, Python, Batch scripting, or similar automation tools

Experience supporting SQL Server, writing SQL queries, and troubleshooting database issues

Experience with AutoSys or similar enterprise scheduling tools

Experience with SFTP, WinSCP, FileZilla, and Windows Scheduled Tasks

Strong networking fundamentals and troubleshooting skills

Excellent analytical, communication, and problem-solving abilities

Highly Preferred

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Wealth Management

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Capital Markets

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Financial Services

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FinTech

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Enterprise Production Support

Nice to Have

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IIS and web application hosting

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SSL/TLS certificate management

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CI/CD or application deployment experience

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ITIL processes

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Experience in highly regulated enterprise environments

Screening Questions

Please be prepared to answer the following:

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Do you have experience monitoring Windows Server and SQL Server performance? Which tools have you used?

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How much experience do you have with IIS and web application hosting?

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How would you rate your PowerShell skills (1–10)? (Looking for 8+)

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Have you deployed or upgraded enterprise Windows applications?

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Have you created, modified, or supported AutoSys (or similar) batch jobs?

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Do you have experience managing SSL/TLS certificates, including renewals and troubleshooting?

Why Join?

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Work with a collaborative, highly technical team.

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Support enterprise-scale applications and infrastructure.

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Hybrid work environment (Downtown Toronto).

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Exposure to modern automation and enterprise technologies.

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Competitive compensation and benefits.

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Excellent opportunities for professional growth.

Apply: sasha@talenttohire.comif you have strong experience with Windows Server, PowerShell, Python,SQL Server, AutoSys, SFTP, and enterprise Application Support, and are ready to make an impact in a mission-critical Financial Services environment.

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