Desktop Systems Administrator II

Join us in bringing joy to customer experience.  Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide.
Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. The Desktop Systems Administrator II serves as an advanced Tier II escalation point, responsible for deploying, maintaining, and supporting enterprise endpoint hardware, operating systems, and core productivity applications.

This role partners closely with Service Desk and Infrastructure teams to ensure high availability, streamline standard operating procedures, and deliver white-glove technical support to on-site, remote, and executive personnel. This position requires being in the office 5 days per week at our Dallas, TX location.

Key Responsibilities Technical Support & VIP Services Tier II Incident Resolution:
Act as an escalation point for complex incidents and service requests from the Service Desk, troubleshooting hardware, software, VPN, mobile devices, peripherals, and network connectivity across Windows and macOS environments.

Executive & VIP Support:
Deliver high-touch, urgent technical support for senior leadership and administrative staff with minimal business disruption.

Incident & Outage Management:
Monitor, prioritize, and resolve ticketing queues within established SLAs; participate in an on-call rotation to resolve critical after-hours incidents and outages.

Event & AV Support:
Configure, test, and facilitate audio/video conferencing solutions (e.g., Zoom Rooms, Microsoft Teams, etc.) for executive presentations and company-wide meetings.

Working with IT Engineering teams, act as “smart hands and eyes” for in-office infrastructure including networking equipment and servers

Endpoint & Systems Administration Endpoint Provisioning & Deployment:
Deploy, configure, and maintain laptops, desktops, and mobile devices using enterprise management tooling (e.g., Intune, Jamf, SCCM).Identity & Access Management:
Administer user accounts, groups, and device policies within Microsoft Entra  (Azure AD) and Okta.

Task Automation:
Familiarity with technologies to automate repetitive administrative workflows and system maintenance tasks through scripting or AI.Infrastructure Relocations:
Coordinate and execute IT workspace setups, office reconfigurations, and moves/adds/changes.

IT Asset Lifecycle Management (ITAM)
Hardware Lifecycle Operations:
Maintain the end-to-end hardware lifecycle, including procurement staging, bench testing, provisioning, secure data sanitization/wiping, and e-waste disposal.

Inventory Control:
Monitor and maintain stock levels for hardware, peripherals, and accessories across local depots in alignment with organizational standards.

Process Improvement & Knowledge Management SOP Development:
Document standardize operating procedures, knowledge base articles, and end-user self-service guides to increase First Contact Resolution (FCR) rates.

Cross-Functional Collaboration:

Partner with Infrastructure, Security, and Desktop Engineering teams to identify operational gaps, rollout technology updates, and enforce IT standards.

Qualifications & Requirements Required Experience & Education

Education & Experience:

Bachelor’s degree in Information Technology, Computer Science, or equivalent practical experience with 5+ years of progressive end-user computing / desktop support experience.

Executive Support:
Minimum 2 years of experience providing dedicated VIP / executive-level technical support.

Operating Systems & Software:
Deep administration knowledge of Windows and macOS, along with enterprise suites (Microsoft 365, Google Workspace, Adobe Creative Cloud, Slack, Zoom).Endpoint Management:
Comprehensive knowledge administering devices via MDM/UEM platforms (e.g., Microsoft Intune / Endpoint Manager, Jamf Pro, or SCCM).Identity & Directory Services:
Practical experience managing users, access permissions, and device compliance in Microsoft Entra  (Azure AD) and Okta.

Networking Fundamentals:
Strong comprehension of enterprise network protocols and services (TCP/IP, DNS, DHCP, VPN, Wi-Fi 802.1x).Communication & Professionalism:
Outstanding written and verbal communication skills; proven ability to translate complex technical concepts into clear, accessible language for non-technical…