Senior IT Systems Engineer

Headquarters: Remote • Canada About Upsun Upsun is the software factory for human-AI workflows. We give teams one unified platform to create, review, deploy, and run software, with AI agents and humans working in sync. Developers, DevOps engineers, and platform teams use Upsun to build and ship with confidence, without wrestling with infrastructure. Upsun brings this together through two products: one that shapes the work, and one that runs it. • Upsun Dispatch™: the AI-first product accelerator. Dispatch governs and simplifies collaboration between AI agents and cross-functional human teams, so work gets shaped, reviewed, and moved to production faster. Ship better code, not just more code. • Upsun Cloud: the Cloud Application Platform for AI acceleration. Cloud is where that software runs. It helps organizations launch agentic software into production confidently and reliably, with: • Predictable performance, even at scale • Secure, compliant environments by default • Real-time observability and profiling built in • Cloning, configuration, and provisioning in seconds • Sandbox environments where AI agents can build and test safely The name says it all. "Up" means uptime, reliability, and acceleration. "Sun" reflects our follow-the-sun-support, a 24x7, globally distributed support team keeping the lights on while you rest. Our core belief is that software should power brighter solutions and greater innovation. What's our commonality, our cultural fabric? A curious spirit and a thirst for knowledge; an eagerness for innovative ideas and cultures. We believe we can build anything together in an environment that frees you to do your best work. Our values: We make a positive impact. We aim for the stars. We care for each other. Impact of a Senior IT Systems Engineer As a Senior IT Engineer, you help shape and improve the systems that our 250+ person remote company relies on every day. Your work spans identity and access, Google Workspace, device management, and our wider SaaS environment. Reporting to the IT Director, you take ownership of complex problems and lead improvements from initial assessment through delivery. You identify what needs attention, recommend priorities, and make thoughtful decisions that balance security, reliability, and employee experience. You also help the team build stronger practices through clear documentation, shared knowledge, and practical guidance. What to expect • Identity platform: Improve our identity and access services, with Okta at the core. This includes single sign-on, automated account provisioning, multi-factor authentication, access policies, and emergency access. Work with IT and Security to make access secure, consistent, and straightforward. • Google Workspace: Lead the administration and improvement of our Google Workspace environment, including users, groups, Gmail, Drive, shared drives, and security settings. Improve how people collaborate, manage sharing and access, and keep our configuration aligned with business needs. • Device management: Help lead the rollout and ongoing development of JumpCloud and our device management practices across macOS, Windows, and Linux. Define and implement device configurations, security policies, software deployment, and onboarding processes in partnership with IT Operations and Security. • Automation and employee lifecycle: Design and improve onboarding, role changes, and offboarding across identity, devices, and SaaS tools. Use tools such as Okta Workflows, n8n, Python, and APIs to reduce manual work and make processes more reliable. • Continuous improvement: Assess our current systems, identify gaps, and turn findings into practical improvements. Investigate complex issues across connected services, address root causes, and