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Job Title


Technical System Administrator


Company : Psiphon


Location : Toronto,


Created : 2026-01-09


Job Type : Full Time


Job Description

About Us: We are a 60-person open source software company building tools that developers love. Our team values transparency, collaboration, and technical excellence. We contribute to and maintain projects used by thousands of developers worldwide, and we practice what we preachrunning our own infrastructure on open source technologies wherever possible. About the Role: We''re looking for a curious, hands-on Technical System Administrator to own and evolve our internal infrastructure, security posture, and developer tooling. You''ll be the go-to person for keeping our systems running smoothly, our team productive, and our data secure. This role requires deep technical knowledge, a love of problem-solving, and the flexibility to wear many hats in a growing organization. You''ll work closely with engineering teams, support our remote and hybrid workforce across multiple platforms, and have significant autonomy to improve how we operate. If you enjoy diving deep into technical problems, automating away toil, and building systems that just work, we''d love to hear from you. Key Responsibilities: Infrastructure & Systems Manage and maintain Linux-based server infrastructure, including containerized workloads using Docker and Podman Administer macOS, Windows, Android, and iOS endpoints across the organization Design, deploy, and troubleshoot network infrastructure including routing, NAT traversal, VPNs, and wireless networking Implement and maintain infrastructure-as-code practices using Git for version control and documentation Security & Access Management Implement and manage network security using firewalls, nftables, and iptables Administer identity and access management systems, including LDAP directories and OAuth/OIDC integrations Deploy and manage Mobile Device Management (MDM) solutions for company and BYOD devices Conduct security assessments and implement best practices for endpoint and network security Manage user provisioning, access controls, and offboarding procedures Operations & Support Provide technical support to staff, troubleshooting hardware, software, and connectivity issues Monitor system performance, availability, and security; respond to incidents as needed Document systems, procedures, and runbooks; maintain an internal knowledge base Evaluate and recommend new tools and technologies that align with our open source values Manage vendor relationships for hardware, software, and services Required Qualifications: Technical Skills Strong experience administering Linux systems in production environments Hands-on experience with container technologies (Docker, Podman, and container orchestration) Solid understanding of IPv4 networking, routing protocols, NAT traversal, and network troubleshooting Experience implementing network security using nftables, iptables, or similar firewall technologies Proficiency with wireless networking standards, configuration, and troubleshooting Experience managing macOS, Windows, Android, and iOS devices in an enterprise context Working knowledge of MDM platforms (e.g., Jamf, Kandji, Intune, or open source alternatives) Strong understanding of authentication protocols and systems: LDAP, Active Directory, OAuth 2.0, SAML, and SSO implementations Proficiency with Git for configuration management, documentation, and collaboration Soft Skills & Mindset Genuine curiosity and a drive to understand how things work at a deep level Excellent problem-solving skills and a methodical approach to troubleshooting Strong written and verbal communication skills; ability to explain technical concepts to non-technical colleagues Self-directed with the ability to prioritize and manage multiple projects Comfortable with ambiguity and adaptable to changing priorities in a growing company Collaborative mindset with a service-oriented approach to supporting colleagues Preferred Qualifications: Experience working at or supporting an open source software company Contributions to open source projects (personal or professional) Experience with configuration management tools (Ansible, Puppet, Salt, or similar) Familiarity with CI/CD pipelines and developer tooling Experience with cloud platforms (AWS, GCP, Azure) and hybrid infrastructure Knowledge of Zero Trust security architectures Scripting proficiency in Bash, Python, or similar languages Experience with monitoring and observability tools (Prometheus, Grafana, ELK stack) Familiarity with compliance frameworks relevant to software companies What We Offer: Competitive salary and benefits package Flexible work arrangements (remote/hybrid options) Opportunity to work with and contribute to open source technologies Professional development budget for conferences, training, and certifications Collaborative, low-ego culture that values learning and experimentation Direct impact on company infrastructure and security practices To Apply: Please submit your resume and a cover letter explaining what excites you about this role and your experience with the technologies listed above. Job Type: Full-time Pay: $70,000.00-$100,000.00 per year Benefits: Casual dress Dental care Extended health care On-site parking Paid time off RRSP match Vision care Wellness program Work Location: Hybrid remote in Toronto, ON M4Y 2E4