Senior Windows Server Automation Engineer in Toronto

This role is temporarily eligible for a pay premium above the posted salary range that is reassessed annually. You are encouraged to have an open dialogue with your recruiter who can provide more specific pay details for this role.

TD is committed to providing fair and equitable compensation opportunities to all colleagues. Growth opportunities and skill development are defining features of the colleague experience at TD. Our compensation policies and practices have been designed to allow colleagues to progress through the salary range over time as they progress in their role. The base pay actually offered may vary based upon the candidate's skills and experience, job-related knowledge, geographic location, and other specific business and organizational needs.

The Senior Windows Server Automation Engineer combines deep enterprise Windows Server engineering expertise with substantial hands‑on experience independently designing, developing, testing, debugging, and maintaining production automation code using Ansible and/or Python.

Key areas of responsibility include:

• Group Policy, Active Directory, Windows Server security baselines, and end‑to‑end server lifecycle management, including OS deployment across physical and virtual environments, initial server configuration, compliance, performance optimization, and ongoing management.
• Success in this role requires demonstrated ownership of complex server platforms and reusable automation solutions throughout their lifecycle.

Key Accountabilities:

• Design, develop, and maintain reusable, production‑grade automation using Ansible and/or Python for OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, patch readiness, and transition to ongoing management.
• Apply sound software‑engineering practices, including modular and idempotent design, source control, testing, logging, error handling, secrets protection, rollback, code review, and CI/CD; use PowerShell where appropriate for Windows Server integration.
• Integrate automation with APIs, orchestration platforms, configuration‑management systems, CMDB, and enterprise service‑management platforms.
• Define and maintain engineering standards and supportable patterns for secure, scalable Windows Server platforms across physical, virtual, and hybrid environments throughout the server lifecycle.
• Design, implement, troubleshoot, and automate enterprise Group Policy and Windows Server security baselines, using Active Directory structures and controls to support targeted deployment, impact analysis, compliance validation, drift detection, exception handling, and remediation.
• Lead Windows Server performance analysis and optimization, complex troubleshooting, and root‑cause resolution across operating system, hardware, virtualization, storage, networking, identity, security, and automation dependencies.
• Own technical designs and production outcomes, review code, mentor engineers, and communicate decisions, risks, and dependencies across infrastructure, security, application, and operations teams.

Experience & Education:

• Required Qualifications:
• Automation Development: Substantial experience independently designing, developing, testing, debugging, and maintaining reusable, production‑grade automation code using Ansible and/or Python, with PowerShell applied as appropriate for Windows Server automation and integration.
• Server Lifecycle Management: Proven experience automating OS deployment across physical and virtual environments, including initial server configuration, domain integration, security hardening, compliance validation, and ongoing management.
• Windows Server Engineering: 8+ years of hands‑on experience engineering and supporting large, complex enterprise Windows Server environments across physical, virtual, and hybrid platforms.
• Group Policy, Active Directory, and Security Baselines: Advanced experience designing, implementing, troubleshooting, and managing enterprise Group Policy, including inheritance, precedence, security and WMI filtering, delegation, controlled rollout, and policy conflict resolution.
• Networking: Working knowledge of TCP/IP, IPv4/IPv6, subnetting, routing, VLANs, DNS, DHCP, firewalls, load balancers, ports, and protocols, with the ability to diagnose Windows Server connectivity, name‑resolution, latency, packet‑loss, and access issues.
• Performance Optimization: Experience baselining, analyzing, and tuning Windows Server CPU, memory, storage I/O, network, services, processes, and virtualization performance using tools such as PerfMon, Resource Monitor, and Windows Performance Recorder/Analyzer.
• Core Windows Infrastructure: Strong knowledge of Kerberos, certificates, failover clustering, server hardware, patching, and vulnerability remediation.
• Senior‑Level Ownership: Demonstrated ability to lead complex designs and production issues independently, make sound technical decisions, provide Level 3 escalation support, and deliver durable solutions across multiple teams.
• Preferred Qualifications:
• Bachelor’s degree in Computer Science, Information Technology, Engineering, or equivalent relevant experience.
• Relevant Microsoft, Red Hat Ansible, or Python certification.
• Experience with VMware, Hyper‑V, cloud platforms, and regulated enterprise environments.

Who We Are:

TD is one of the world's leading global financial institutions and is the fifth largest bank in North America by branches/stores. Every day, we strive to make every interaction, product, and experience remarkably human and refreshingly simple for over 27 million households and businesses in Canada, the United States and around the world. More than 95,000 TD colleagues bring their skills, talent, and creativity to foster deeper relationships, ensure disciplined execution, and build a simpler, faster banking experience.

Our Total Rewards Package reflects the investments we make in our colleagues to help them and their families achieve their financial, physical, and mental well‑being goals. Total Rewards at TD includes a base salary, variable compensation, and several other key plans such as health and well‑being benefits, savings and retirement programs, paid time off, banking benefits and discounts, career development, and reward and recognition programs.

We’re delighted that you’re considering building a career with TD. Through regular development conversations, training programs, and a competitive benefits plan, we’re committed to providing the support our colleagues need to thrive both at work and at home.

Please be advised that this job opportunity is subject to provincial regulation for employment purposes. It is imperative to acknowledge that each province or territory within the jurisdiction of Canada may have its own set of regulations, requirements.

If you’re interested in a specific career path or are looking to build certain skills, we want to help you succeed. You’ll have regular career, development, and performance conversations with your manager, as well as access to an online learning platform and a variety of mentoring programs to help you unlock future opportunities.

If you’re passionate about helping clients and building deep, lasting relationships, TD offers diverse career paths where you can grow your expertise and make a meaningful impact.

We're committed to your success and foster a respectful workplace where diverse perspectives are valued, everyone has fair opportunities to grow, and you can unlock your full potential to achieve your career goals. Here at TD, we hire and develop the best.

We will provide training and onboarding sessions to ensure that you’ve got everything you need to succeed in your new role.

We’ll reach out to candidates of interest to schedule an interview. We do our best to communicate outcomes to all applicants by email or phone call.

Your accessibility is important to us. Please let us know if you’d like accommodations (including accessible meeting rooms, captioning for virtual interviews, etc.) to help us remove barriers so that you can participate throughout the interview process.

We look forward to hearing from you!