Information Systems Engineer

Location: Toronto, Canada (in-person four days per week)

Opendoor's mission is to empower everyone with the freedom to move. We are building a digital, end-to-end experience that makes buying and selling a home simple, certain, and fast. Our IT team drives that mission from the inside, designing, scaling, and securing modern systems through automation and engineering excellence so every team can move faster with confidence. We are looking for an Information Systems Engineer to lead the evolution of our IT infrastructure across SaaS platforms, cloud environments, and endpoints. You will build automation, strengthen access controls, and design the tools that let every employee work efficiently and securely.

Systems Engineering & Automation

• Lead the design, implementation, and maintenance of secure, scalable IT infrastructure across SaaS, cloud, and endpoint environments.
• Administer and optimize core platforms including Google Workspace, Slack, Microsoft 365, Jamf, Intune, and related tooling.
• Manage cloud infrastructure touchpoints across AWS, Azure, and GCP, ensuring secure and reliable integration with IT systems.
• Troubleshoot and maintain office networks using Meraki and a unified network stack.
• Build and maintain automation scripts in Python, Bash/Zsh, and PowerShell to eliminate manual overhead.
• Design repeatable, version controlled systems management workflows; leverage Infrastructure as Code principles.
• Develop robust onboarding and offboarding automation that spans device provisioning, SaaS account lifecycle, and access workflows.

Project Execution & Collaboration

• Lead and participate in IT projects end to end — planning, design, implementation, testing, and documentation.
• Manage project timelines and deliverables with precision; communicate status clearly to stakeholders and leadership.
• Drive cross-functional initiatives that align IT with the organization's broader strategic goals.
• Partner closely with Security, Engineering, Finance, HR, and other business units.
• Align IT engineering work with compliance requirements and organizational risk posture.

Team Leadership & Mentorship

• Serve as a technical escalation point for junior IT engineers and IT operations technicians.
• Mentor team members on best practices in systems administration, automation, and documentation.
• Maintain detailed, up-to-date documentation of systems, configurations, processes, and runbooks.
• Proactively monitor system health, logs, and metrics to anticipate and prevent outages or compliance drift.

Tech Stack

Google Workspace, Slack, Microsoft 365, Jamf, Intune, Entra ID, AutoPilot, Okta, AWS, Azure, GCP, Meraki, Python, Bash/Zsh, PowerShell, Terraform.

What You'll Need

• Deep conviction that AI and automation should eliminate manual work, with a proven track record building automated lifecycle systems that replace manual toil, not click-ops.
• Track record owning IT engineering work end to end, including projects.
• Strong hands-on experience administering SaaS platforms such as Google Workspace, Slack, Microsoft 365, Jamf, and Intune.
• System administration across macOS and Windows endpoints, including Windows management with AutoPilot, Intune, and Entra ID.
• Working knowledge of modern identity protocols (SAML, OAuth, OIDC, SCIM) and integrations across them.
• Scripting in Python, Bash/Zsh, and PowerShell.
• Working knowledge of cloud infrastructure across AWS, Azure, and/or GCP.
• Product mindset: infrastructure like code, end users like customers.
• Security mindset: guardrails in code, the secure path is the fast path.

Bonus Points

• Relevant certifications such as Google Workspace Admin, CISSP, CompTIA, or equivalent.
• Scaled IT systems in fast-paced, high-growth, or multi-entity environments.
• Led projects spanning multiple teams or departments.