It is built for today’s hybrid teams, where AI agents write and test code and humans focus on solving the problems that really matter. Developers, DevOps engineers, and platform teams use Upsun to build, ship, and scale confidently without wrestling with backend infrastructure. Predictable performance, even at scale Cloning, configuration, and provisioning in seconds AI-ready features that plug directly into your stack Sun” reflects our follow-the-sun-support, a 24×7, globally distributed support team keeping the lights on while you rest.

Our core belief is that software should power brighter solutions and greater innovation. Upsunners are a remote, global workforce, and we thrive in a multicultural team. 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.

Reporting to the IT Director, you take ownership of complex problems and lead improvements from initial assessment through delivery. You also help the team build stronger practices through clear documentation, shared knowledge, and practical guidance. 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. Improve how people collaborate, manage sharing and access, and keep our configuration aligned with business needs. 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. Use tools such as Okta Workflows, n8n,



Python, and APIs to reduce manual work and make processes more reliable.

Continuous improvement: Administer our core internal tools and help evaluate new applications. Partner with Security and the Risk and Audit team to implement and maintain controls across identity, Google Workspace, devices, and SaaS tools. Automate evidence collection where practical to support ISO 27001 and SOC 2 Type 2.

Project delivery and mentoring: Lead projects from scoping and technical design through rollout and handover. Coordinate dependencies, communicate risks and progress, and help colleagues grow through documentation, reviews, and knowledge sharing.

Broad IT engineering experience: You understand how these systems connect and can troubleshoot problems across them. ~ Device management deployment: You have helped deploy or significantly improve an MDM or endpoint management platform. You can turn security and operational requirements into workable configurations, test them, and roll them out with minimal disruption. You build reliable automation using workflow tools, APIs, webhooks, and Python or a comparable scripting language.

You consider error handling, monitoring, and ongoing maintenance. You can share examples of systems or processes you assessed, improved, and delivered, with clear results for employees or the IT team. You work independently,



make sound technical decisions, and know when to involve others.

You have implemented controls such as access reviews, secure configurations, or device policies, and understand how to document and demonstrate that they work. You work effectively in a fully remote team and communicate clearly with technical and non-technical colleagues across cultures. You share knowledge and help others become more effective.

Typically six or more years in IT engineering, systems administration, identity, or endpoint management, with increasing responsibility for technical decisions and project delivery. At Upsun, work from home isn’t just a trend – it’s our foundation. The freedom of remote work with the support of a diverse, global team has been our successful model for over a decade.

Our culture celebrates flexibility and collaboration, and while we have team members in over 30 countries around the globe, we are currently focused on hiring for this role in Canada, France, Germany, Spain, and the United Kingdom . Although we’re unable to provide visa sponsorship at this time, we welcome applications from all qualified candidates who are legally authorized to work in these countries. A product you can believe in – Join us in transforming how businesses build and manage web applications, driven making a positive impact as a proud B Corp .

An Award-Winning Workplace – We’ve been recognized by Forbes’ Top 30 Companies for Remote Jobs and France’s Best Workplaces for Women. A culture that values your voice – Join a flexible, open, and inclusive work environment where your voice is encouraged, and your ideas shape our growth and evolution.

📌 Senior IT Engineer, Systems Engineering (Winnipeg)
🏢 Webhosting
📍 Winnipeg