Senior System Administrator III
Job Description
Overview:
The Senior System Administrator is a highly experienced technical leader within the Sterling IT team, responsible for ensuring the reliable operation, modernization, and security of the company’s core systems and cloud platforms. This is not an entry-level role; it requires expert-level administration of Microsoft 365, cloud identity (Entra), Exchange Online, SharePoint, Intune, Windows Autopilot, Meraki networking, Cisco Firewalls and VMware virtualization.
You will play a key role in Sterling’s IT evolution, partnering with Yardi System Administrator to form the Systems Administration pillar of the IT department. This role demands extreme ownership, excellent communication skills, and the ability to proactively drive technical projects to completion in a fast-paced, high-performance environment.
To learn more about the company, please visit our website sterlingorganization.com.
Primary Responsibilities:
- Ownership of the System Administration Pillar of the Sterling IT Department
- Administration of Microsoft 365, Exchange Online, Entra ID, SharePoint, OneDrive, Teams, Microsoft Copilot and other SaaS platforms
- Designing and enforcing Intune, Autopilot, and Conditional Access policies for device management
- Administration of VMware vSphere virtual environments, including NAS storage and backup strategy using Veeam
- Collaborating with Helpdesk Manager, Cyber Security Manager and Yardi System Admin
- Administration of Meraki networking devices and Cisco Firepower firewalls, including VPN
- Monitor logs, alerts, and service dashboards for performance, uptime, and security
- Serve as Tier III escalation point for support issues and access requests
- Evaluate new platforms or services and lead their secure implementation upon approval
- Create and maintain documentation for systems, policies, and SOPs
- Ensure all systems are patched, secured, and optimized regularly
- Assist in preparing materials and responses for IT audits, vendor due diligence, investor evaluations, and disaster recovery testing, ensuring all systems meet compliance standards
- Collaborate across departments to align IT tools with business goals, provide solutions and answer technical questions
Specific Knowledge, Skills and Abilities:
- Team-first mindset, extreme ownership of systems under your care with minimal oversight
- Microsoft 365 (Admin Center, SharePoint, Teams, OneDrive, Copilot)
- Microsoft Windows Server 2016, 2019, 2022 Setup, Configuration and Administration
- Microsoft Entra ID (formerly Azure AD), Active Directory, DNS, DHCP
- Intune, Autopilot, Defender, and Conditional Access policy creation
- VMware vSphere, Veeam, enterprise NAS administration
- Meraki (MX, MR, MS), Cisco Umbrella, Firepower, AnyConnect VPN, VLAN setup and troubleshooting
- Zoom VOIP platform
- Proofpoint Email Security
- Remote tools (ConnectWise, RDP, SSH)
- Microsoft Office products such as Word, Excel, Outlook, Visio and PowerPoint
- Hardware upgrades, OSI model, Linux CLI experience, Windows event log review
General Knowledge, Skills and Abilities:
- Knowledge of enterprise-level storage, management, backup and security methodology
- Knowledge of TCP/IP, network ports, network designs, network monitoring and tools
- Knowledge of technical writing principles and practices
- Knowledge of compliance requirements, including SEC and SOX
- Understanding of how to implement and record a disaster recovery plan
- Understanding of the Principle of least Privilege
- Understanding of the CIS benchmarks and NIST security framework
- Strong detail-oriented, systematic troubleshooting and problem-solving skills and can keep calm under tight time constraints and high pressure.
- Strong and personable communication skills, including verbal, face-to-face, written, presentation, end-user training, and leadership reporting, ability to work well with a team
- Self-starter with ability to quickly learn and apply new concepts, principles and solutions
- Willingness to be flexible and adaptable to fast-changing priorities and schedules
- Maintain effective working relationships with employees, vendors and supervisors
- Strong understanding of customer service methods and theory
- Experience reading and creating technical drawings and network maps
Minimum Experience & Qualifications:
- 10+ years of IT experience (hardware, software, systems)
- 6+ years of Microsoft 365 and cloud/SaaS platform administration
- 6+ years in VMware, storage, backup, and server infrastructure
- 4+ years in customer service, project, or leadership context
- Experience leading IT projects and supporting modernization initiatives
- Previous experience in an enterprise-level IT environment
- Strong documentation, communication, and team collaboration history
- Associate’s degree or higher (or equivalent coursework)
- Clean criminal record, valid driver's license
Certifications (Required or Equivalent Experience):
- CompTIA A+, Network+, Security+, ITIL Foundation, CompTIA Project+
- Microsoft 365 Administrator or Endpoint Administrator Associate, Microsoft Certified: Identity and Access Administrator Associate, Microsoft Certified: Information Protection and Compliance Administrator Associate, MCSA, MCSE
- VMware VCP or comparable virtualization certification
- Cisco CCNA
Workplace Expectations:
- Reports onsite in West Palm Beach; occasional after-hours support required
- Serves as a technical lead for infrastructure and M365-related platforms
- Collaborates directly with the IT Team to deliver company-wide improvements
- Maintains high availability standards across all supported systems (target: 99.7% uptime)
- Maintains up-to-date certifications and pursues at least one new relevant certification per year
Benefits:
- Employer-paid certification testing and renewals, online technical training
- Medical, dental, vision, life, disability insurance and 401(k) match
- Onsite Gym
- Paid holidays and vacation
- High-impact, visible role in a growing, high-performance IT team
Sterling Organization is an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender identity, sexual orientation, national origin, ethnicity, age, disability, veteran status, marital status, or any other characteristic protected by law.