Upsun: Senior IT Systems Engineer

Upsun: Senior IT Systems Engineer

Headquarters: Remote • Canada Source: weworkremotely

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:

• Upsun Dispatch™: The AI-first product accelerator. Dispatch governs and simplifies collaboration between AI agents and cross-functional human teams.
• Upsun Cloud: The Cloud Application Platform for AI acceleration. It helps organizations launch agentic software into production with predictable performance, secure environments, real-time observability, and rapid provisioning.

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.

What to Expect

• Identity platform: Improve our identity and access services, with Okta at the core (SSO, automated provisioning, MFA, access policies).
• Google Workspace: Lead the administration and improvement of our Google Workspace environment, including users, groups, Gmail, Drive, and security settings.
• Device management: Lead the rollout and development of JumpCloud and device management practices across macOS, Windows, and Linux.
• Automation and employee lifecycle: Design and improve onboarding, role changes, and offboarding using tools like Okta Workflows, n8n, Python, and APIs.
• Continuous improvement: Assess current systems, identify gaps, and address root causes.
• SaaS administration and governance: Administer core internal tools and establish practices for application setup, integrations, and access reviews.
• Security and compliance: Partner with Security and the Risk/Audit team to maintain controls (ISO 27001 and SOC 2 Type 2).
• Project delivery and mentoring: Lead projects from design through rollout and help colleagues grow through documentation and knowledge sharing.

What You Bring

• Broad IT engineering experience: Hands-on experience across identity, collaboration tools, endpoint management, and SaaS administration.
• Depth in a core area: Strong expertise in at least one of Okta, Google Workspace, or JumpCloud.
• Device management deployment: Experience deploying or improving an MDM or endpoint management platform.
• Automation and scripting: Ability to build reliable automation using workflow tools, APIs, webhooks, and Python or similar languages.
• A track record of improvement: Proven ability to assess, improve, and deliver systems with clear results.
• Proactive judgment and ownership: Ability to work independently, make sound technical decisions, and manage trade-offs.
• Security and compliance awareness: Experience implementing controls and supporting ISO 27001 or SOC 2.
• Clear communication: Ability to work effectively in a fully remote, multicultural team.
• Experience: Typically 6+ years in IT engineering, systems administration, identity, or endpoint management.

Bonus Points

• Experience supporting mergers and acquisitions.
• Experience in a developer-heavy or engineering-led company.
• Experience supporting both ISO 27001 and SOC 2 Type 2, including automated evidence collection.
• Professional proficiency in French.

Where We Hire

Upsun is a global, remote-first workforce. We are currently hiring for this role in Canada. We are unable to provide visa sponsorship at this time, but we welcome applications from all qualified candidates who are legally authorized to work in Canada.

How We Hire

Our interview process consists of 4 interviews on Google Meet:

1. 45 Minutes with Talent Acquisition
2. 60 Minutes with Hiring Manager (Director, IT)
3. 60 Minutes with Team (Senior Director, Site Reliability Engineering, Senior IT Manager)
4. 45 Minutes with Executive (Senior Director, FP&A & IT)

All roles require background checks.

What We Offer

• A product you can believe in: Join us in transforming how businesses build and manage web applications as a proud B Corp.
• An Award-Winning Workplace: Recognized by Forbes’ Top 30 Companies for Remote Jobs and France’s Best Workplaces for Women.
• A culture that values your voice: A flexible, open, and inclusive work environment.
• A global team: Collaborate with colleagues from diverse backgrounds across the world.
• Benefits and perks:
  • Flexible PTO
  • Comprehensive healthcare coverage
  • Company stock options
  • Professional development budget
  • Office equipment budget
  • Wellness budget
  • Annual team gatherings
  • Inclusive parental leave
  • Remote work travel program

You Belong Here

At Upsun, we celebrate diversity and are committed to fostering an inclusive, equitable, and supportive workplace. If you need accommodations at any stage of our hiring process, please let us know.

To apply: Click here to apply via We Work Remotely