Staff Systems Engineer - Endpoint Management (Windows)


We are looking for a Windows expert with a passion for designing and running complex cloud-based, desktop, and server infrastructure and endpoints to join Okta’s Endpoint Management team.  In this role you will be part of the Business Technology (BT) Engineering Services team, focused on Windows management and security.  You will be responsible for ensuring the security, usability, and deployment of all Windows-based endpoints at Okta, including PCs used by employees and virtual machines hosted in AWS Workspaces. This will include building and automating processes and workflows to create VMs as Okta expands its usage of virtualized workstations for Federal compliance and more.

We are a team of smart and innovative engineers who welcome challenges and enjoy seeing our designs run at scale with automation, testing, and tuning.  Above all, we are a team who touches every point of the business and are obsessed with user experience.


  • Manage Okta’s fleet of Windows PCs globally with VMware Workspace ONE
  • Create workflows, pipelines, and images for Windows-based virtual machines in a VDI ecosystem
  • Ensure that Windows VMs meet regulatory requirements (ex: FedRAMP, NIST, STIG, etc.)
  • Deploy and update applications, configurations, settings, and scripts to all Windows endpoints, and keep devices up to date as new vulnerabilities are discovered
  • Secure all Windows endpoints to meet CIS standards, following industry best practices to protect Okta data
  • Collaborate with other BT teams to automate provisioning, deprovisioning, and support procedures for Windows endpoints
  • Plan and prepare for future growth and scaling of the Windows program at Okta, including the expansion of the Federal program and future acquisitions/integrations.
  • Advocate for Okta employees using Windows devices and provide them with the best user experience possible


  • Expertise managing the Windows OS and Windows-based applications
  • Experience with VMware Workspace ONE or other Windows management platforms
  • Experience with VDI technologies and tools, especially with ephemeral instances
  • Proficient in PowerShell scripting and automation
  • Experience building and integrating Okta into Windows Management Systems
  • Knowledge of AWS (Workspaces, Systems Manager, Directory Services)
  • Understanding of CIS Benchmarks and endpoint hardening best practices
  • Experience with Federal requirements and FedRAMP compliance
  • Knowledge of SAML authentication and federation workflows
  • Good communication and writing skills, specifically technical documentation
  • Experience in defining/generating reports and metrics

((Colorado, New York and Washington only*) Minimum OTE of $154,000/year + bonus + equity + benefits))

Okta is an Equal Opportunity Employer.

Okta is rethinking the traditional work environment, providing our employees with the flexibility to be their most creative and successful versions of themselves, no matter where they are located.  We enable a flexible approach to work, meaning for roles where it makes sense, you can work from the office, or from home, regardless of where you live.  Okta invests in the best technologies and provides flexible benefits and collaborative work environments/experiences, empowering employees to work productively in a setting that best and uniquely suits their needs.  Find your place at Okta 

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