Remote Systems Administrator

Upwork ($UPWK) is the world’s work marketplace. We serve everyone from one-person startups to over 30% of the Fortune 100 with a powerful, trust-driven platform that enables companies and talent to work together in new ways that unlock their potential.

Last year, more than $3.8 billion of work was done through Upwork by skilled professionals who are gaining more control by finding work they are passionate about and innovating their careers.

This is an engagement through Upwork’s Hybrid Workforce Solutions (HWS) Team. Our Hybrid Workforce Solutions Team is a global group of professionals that support Upwork’s business. Our HWS team members are located all over the world.

Upwork Corporate Technology team manages the technical ecosystem for the internal user community. We are seeking an experienced Systems Administrator with 3-5 years of experience to join our team. The successful candidate will have a strong technical background in managing enterprise IT systems, focusing on virtualization, security, cloud environments, and endpoint management. You will be responsible for maintaining, configuring, and ensuring the reliable operation of systems such as VDI, Google Workspace, vulnerability patch management tools, MDM, and more. Proficiency with macOS, Windows, and Linux, as well as proficiency in security tools like Zscaler. Experience with identity management platforms such as Okta and SailPoint, is required. Your role will also provide high-level support and collaboration on technical projects to improve infrastructure stability, performance, and security.

Work/ Project Scope:

• System Administration: Manage and maintain Windows, Linux, and macOS systems, ensuring high availability and performance.

• VDI Management: Oversee the administration and optimization of virtual desktop infrastructure (VDI) environments to support remote users.

• Google Workspace Administration: Administer Google Workspace, including user account management, security policies, and system integrations.

• Patch Management: Implement and manage vulnerability patching processes across all systems and applications, ensuring compliance with security best practices.

• Endpoint Management (MDM): Deploy and manage endpoints using mobile device management (MDM) solutions like Intune, Jamf, etc.

• Identity and Access Management: Administer Okta and SailPoint systems to manage user authentication, authorization, and identity lifecycles.

• Security Management: Implement and monitor security solutions like Zscaler to ensure the integrity and confidentiality of data.

• Helpdesk and Support: Provide Tier ²⁄₃ technical support for escalated user issues.

• Automation and Scripting: Automate routine tasks and system management using Terraform, PowerShell, Bash, Python, or similar scripting tools.

• Project Collaboration: Collaborate with cross-functional teams to support infrastructure-related projects, system upgrades, and migrations.

• Documentation and Reporting: Maintain up-to-date documentation on system configurations, policies, and procedures.

• MacOS Expertise: Provide strong support and system management for macOS users, ensuring seamless integration into the company’s ecosystem.

Must Haves (Required Skills):

•Experience:

•3-5 years of experience in systems administration with a focus on macOS environments, cloud-based services, and VDI solutions.

•Experience with endpoint management (MDM), vulnerability patch management, and system automation.

•Technical Skills:

•Strong expertise in macOS, Windows Server, and Linux systems.

•Hands-on experience with Google Workspace administration and security.

•Experience with VDI environments and management.

•Proficiency with patch management and vulnerability scanning tools.

•Experience with Okta (or similar IAM platforms), SailPoint, Active Directory, and Zscaler for security and identity management.

•Strong understanding of networking (TCP/IP, DNS, DHCP) and firewall management.

•Familiarity with Jira for ticketing and project management.

•Certifications (Preferred but not required):

•Microsoft Certified: Azure Administrator Associate

•CompTIA Network+

•Citrix Certified Professional

•Google Workspace Administrator Certification

•ITIL Foundation Certification

•Strong troubleshooting and problem-solving skills, especially in macOS and enterprise systems.

•Ability to work independently, manage multiple projects, and meet deadlines in a fast-paced environment.

•Excellent communication skills for both technical and non-technical audiences.

•Strong attention to detail and commitment to process improvements and document

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