Remote Windows System Administrator Jobs in Oregon

We are seeking an experienced and driven Senior IT Engineer to serve as a senior technical contributor on Posit's IT Operations team, supporting our distributed workforce, corporate systems, and enterprise AI infrastructure. The ideal candidate is a seasoned systems administrator and support engineer who has moved beyond day-to-day ticket response and is ready to take ownership of critical platforms, lead cross-team technical efforts, and mentor more junior team members. You'll play a leading role in operating our IT infrastructure, raising the bar on our processes and documentation, and ensuring the productivity and security of our employees. IT Operations owns and runs the platforms everything else rides on - identity, endpoints, SaaS systems, the enterprise AI platform, and the infrastructure for our enterprise automation platform. Our department's mission is to empower Posit's employees with reliable technology, maintain a robust IT environment, and operate the platform foundation for the company's enterprise AI program. You will collaborate closely with other teams across the organization to achieve our departmental mission. We achieve this through proactive system management, responsive user support, code-driven operations, and continuous process improvement, enabling innovation with effective IT solutions. Since its inception, Posit has operated as a 100% distributed company with a SaaS-first infrastructure, complemented by select platforms we host and manage ourselves in AWS. This presents unique challenges and requires pragmatism, creativity, and a collaborative, detail-oriented approach to be successful.

• End-to-end ownership of one or more core IT platforms (platforms such as Okta, Google Workspace, Jamf Pro, Zoom, Slack, or the infrastructure for automation platforms such as n8n, Workato, or Okta Workflows) - including configuration, health, security posture, and roadmap. For the automation platform, that means the platform itself - hosting, upgrades, access, backups, and monitoring - while IT Engineering builds the workflows within it. While most of our stack is SaaS, some platforms are self-hosted in AWS, and that infrastructure is ours to run.
• Complex technical escalations across end user devices (Mac, Windows, Linux) and SaaS applications, serving as the senior point of contact when issues exceed the scope of Tier 1 support.
• Design and implementation of meaningful improvements to employee technology workflows - onboarding, offboarding, device lifecycle, access provisioning with scalability at the forefront.
• Day-to-day operational ownership of Posit's enterprise AI platform and its supporting integrations, including SSO/SCIM health, license management, desktop deployment via MDM, and front-line support for complex issues.
• Technical mentorship of IT Engineers - pairing on tickets, reviewing pull requests, and leveling up the team's technical practices.
• Maintenance of SaaS configurations, end user device controls, system access controls, and patch management according to approved guidelines, with a high bar for security and compliance.
• Creation and upkeep of technical documentation, runbooks, and playbooks for the systems and processes you own.
• Leading scheduled audits of IT-controlled systems and coordinating remediation of findings.
• Driving IT's GitOps practice forward - managing meaningful portions of your owned systems through version-controlled code, pull requests, and peer review, and coaching others through the same workflow.

• Defining and refining IT's engineering standards, including IaC patterns, code review expectations, and exception processes.
• Contributing to procurement, vendor evaluation, and technical assessments for new tools - with a clear eye toward automation, support for configuration as code, and integration with our existing stack.
• Enforcing procedures for safeguarding information security and safety within IT procedures.
• Tracking hardware/software assets (licenses, warranties, accounts); identifying capacity and spending trends before they become problems.
• Responding to internal and external audit requests in partnership with GRC and Security.
• Operating and supporting the rollout of approved MCP integrations and AI workflows built by IT Engineering - owning the identity, access, deployment, and monitoring layers they depend on.
• Recommending and implementing IT process improvements, with a bias toward automation over manual toil.

• You have significant progressive IT experience, with meaningful time spent as a system administrator or engineer in a SaaS-first or distributed environment.
• You thrive on solving problems through investigation and deductive reasoning, and you know when to escalate, when to dig in, and when to step back and redesign.
• You invest in strong relationships with your colleagues and employ empathy when working through their technical issues. You can translate complex technical topics for non-technical audiences, and you can hold your own with security, engineering, and legal stakeholders.
• You are self-driven, demonstrate initiative, and maintain a high degree of professional conduct at all times.
• You are highly ethical, possess excellent decision-making capabilities, and execute good time management skills.
• You question assumptions, drive change to mitigate potential risks, and possess excellent documentation skills.
• You have deep working knowledge of corporate technologies - identity providers, MDM platforms, productivity suites, and endpoint security tooling - platforms such as Okta, Jamf Pro, Microsoft Intune, Fleet, Google Workspace, Slack, and Zoom.
• You are highly proficient with multiple versions of macOS, Linux, and Windows operating systems and have hands-on experience administering mobile device management platforms at scale (platforms such as Jamf Pro, Microsoft Intune, or Fleet).
• You have strong working knowledge of authentication and authorization protocols (SAML, OIDC, SCIM), MFA/SSO architectures, and common identity threats.
• Experience in meeting goals in a fast-paced environment with rapidly evolving needs, including ownership of cross-functional projects from planning through delivery.
• You have technical working knowledge and experience administering multiple SaaS applications at scale.
• Experience managing infrastructure in AWS (compute, networking, IAM, backups, and monitoring) is a plus - while most of our stack is SaaS, IT Operations also hosts and manages self-hosted platforms in AWS.
• Hands-on experience with GitOps practices for IT Operations - version control, pull request workflows, and Infrastructure-as-Code platforms such as Pulumi or Terraform - or demonstrated ability to get there quickly with prior scripting/automation experience.
• Familiarity with enterprise AI platforms such as Claude Enterprise, and an understanding of how SSO, SCIM, MDM, and integration platforms combine to operate AI systems safely at scale.

• Complete all HR and IT onboarding processes, familiarizing yourself with Posit's IT systems, security practices, and communication channels.
• Familiarize yourself with Posit products, departments, and strategic goals.
• Build working relationships with key stakeholders across IT Engineering, Security, GRC, and CloudOps.
• Conduct a thorough review of existing IT documentation, tooling, and processes, and surface your first round of observations and recommendations.
• Independently resolve complex end-user support escalations and begin taking over operational responsibility for at least one core IT system.
• Review and contribute to existing GitOps codebases, starting with small, low-risk changes to get comfortable with the workflow.

• Own end-to-end operations for at least one core IT platform, including its security posture, integrations, and roadmap.
• Lead the design and rollout of at least one significant operational improvement - an automation, a new integration, a process simplification - with measurable impact.
• Actively participate in, and help run, hardware logistics, onboarding, and offboarding workflows.
• Mentor IT Engineers, pairing on tickets and reviewing their work.
• Drive meaningful portions of your owned system(s) into Infrastructure-as-Code, making routine changes via pull request rather than console.
• Act as a senior technical responder for enterprise AI platform and MCP-related incidents and escalations.

• Be recognized across the organization as the go-to owner for your core platforms, consistently delivering on operational KPIs (uptime, MTTR, audit readiness, license utilization).
• Have led at least one cross-functional IT project from planning through delivery, working with Security, GRC, and Engineering counterparts.
• Have shaped IT's engineering standards and playbooks - authored or significantly contributed to key runbooks, ADRs, and shared code.
• Play a lead role in audits and compliance activities for the systems you own, with clean findings and automated evidence where possible.
• Be a trusted mentor for more junior team members and a visible champion of GitOps, documentation-as-code, and automation-over-toil inside IT.
• Help plan and deliver the ongoing evolution of Posit's enterprise AI platform - platform readiness for new MCP integrations shipped by IT Engineering, governance improvements, and end-user enablement.