Design, deploy, and support multi-cloud (Azure/AWS) environments with IaC (Terraform/Ansible/Puppet), automation scripting, CI/CD, and security controls. Lead cloud migrations, provide senior-level customer technical support, incident containment, and build AI-enabled knowledge/automation to improve operations and reduce manual work.
Key Responsibilities:
Cloud Infrastructure & Architecture
- Architect, deploy, configure, and support cloud infrastructure on Azure, AWS, and other public clouds for high availability, performance, and security.
- Lead migration of on-premise customer environments to hosted cloud platforms, targeting completion milestones aligned with signed customer commitments and pipeline forecasts.
- Implement and maintain security measures including identity management, network segmentation, and compliance controls across cloud environments.
- Configure secure integrations with external services (OAuth, Microsoft 365, GSuite, third-party applications).
- Optimize cloud resource utilization and cost efficiency, with measurable cost-per-environment targets.
Automation & Scalability
- Develop and maintain Infrastructure-as-Code using Terraform, Ansible, and/or Puppet to enable scalable, repeatable environment provisioning.
- Build toward a fully automated CI/CD pipeline for deployment and monitoring, reducing manual provisioning time by a measurable target (to be established within first 90 days).
- Create automation scripts (Python, Bash, PowerShell) to eliminate repetitive infrastructure tasks.
Technical Support & Customer Engagement
- Serve as primary technical support liaison for hosted and on-premise client environments, delivering resolution within defined SLAs.
- Diagnose and resolve complex customer infrastructure issues across server operating systems (Linux, Windows) and database platforms (SQL Server, MySQL, PostgreSQL, Oracle).
- Document all customer requests, diagnostic steps, and resolutions thoroughly and consistently.
- Communicate progress and status to internal and external stakeholders with frequency and clarity.
AI Strategy & Adoption
- Leverage AI-assisted coding tools (e.g., GitHub Copilot, Claude Code) to accelerate IaC development, scripting, and troubleshooting workflows.
- Build and maintain AI-enabled knowledge bases from existing company knowledge resources, supporting the BU's AI-DLC Level 2/3 roadmap toward customer-facing agents and adjacent software modules.
- Ensure responsible use of AI tools in all internal and customer-facing contexts, specifically regarding data privacy, PII protection, and intellectual property.
- Identify and document at least 2 AI-driven workflow improvements within the first 90 days, with estimated hours saved.
Incident Response & Systems Administration
- Provide priority assistance in containment and remediation during cybersecurity incidents.
- Perform general systems administration including installation, configuration, maintenance, system audits, backups, and patch management.
Qualifications:
- 5+ years of experience in a System/Cloud Administrator role.
- Demonstrated proficiency with Azure and AWS cloud platforms, including environment architecture and deployment.
- Experience with database platforms: Microsoft SQL Server, MySQL, PostgreSQL, and/or Oracle.
- Strong knowledge of networking concepts and technologies.
- Working proficiency across Linux and Windows server operating systems.
- Experience with Infrastructure-as-Code tools (Terraform, Ansible, or Puppet).
- Demonstrated proficiency with AI prompting and working knowledge of LLMs, including when to use them and when not to, with specific attention to privacy and IP considerations.
- Ability to manage competing priorities, triage by urgency, and drive issues to resolution independently.
Preferred Qualifications:
- Proven hands-on experience architecting multi-tenant or multi-customer cloud environments.
- Strong scripting skills in Python, Bash, and/or PowerShell.
- Experience with containerization (Docker) and orchestration (Kubernetes).
- Familiarity with CI/CD pipeline design and DevOps practices.
- Cloud certifications (Azure, AWS) from tier-one providers.
- Experience in a customer-facing technical support role with SLA accountability.
- Prior experience applying AI tools to infrastructure automation or knowledge management workflows.
Salary range: $75,000 - $85,000 CAD per year.
Similar Jobs
Blockchain • Fintech • Mobile • Payments • Software • Financial Services
Leads global ecosystem partnership strategy and commercialization across Cash App, Afterpay, and Square. Builds zero-to-one partnership models, evaluates investments and unit economics, negotiates complex agreements, coordinates product and engineering integrations, and scales successful opportunities globally. Owns portfolio performance, executive relationships, cross-functional priorities, and repeatable partnership practices. Requires deep payments or fintech expertise, strong commercial judgment, and experience influencing senior stakeholders without formal authority.
Top Skills:
B2B PaymentsB2B2C PaymentsPayment IntegrationsPayments Technology
Cloud • Security • Software • Cybersecurity • Automation
Leads complex, multi-workstream professional services programs for strategic customers. Responsibilities include defining delivery methodologies, managing roadmaps, dependencies, budgets, risks, schedules, stakeholders, and milestones; establishing program governance; communicating delivery metrics; and coordinating customer, engineering, security, architecture, and delivery teams. The role supports customer adoption and transformation through structured agile program execution in a remote environment.
Top Skills:
AgileDevsecopsGitlab
Cloud • Security • Software • Cybersecurity • Automation
Leads community growth strategy, member experiences, events, automated journeys, and integrated marketing for GitLab’s community programs. Builds programming calendars, collaborates with Sales, Customer Success, executives, and external partners, and uses AI and analytics to improve membership growth, engagement, retention, advocacy, and account participation.
Top Skills:
AICrm SystemsLifecycle MarketingMarketing AutomationWeb Analytics
What you need to know about the Toronto Tech Scene
Although home to some of the biggest names in tech, including Google, Microsoft and Amazon, Toronto has established itself as one of the largest startup ecosystems in the world. And with over 2,000 startups — more than 30 percent of the country's total startups — Toronto continues to attract new businesses. Be it helping entrepreneurs manage their finances, simplifying business operations by automating payroll or assisting pharmaceutical companies in launching new drugs, the city's tech scene is just getting started.
