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Bear Real Estate Group · 2 months ago

SENIOR IT SYSTEM ADMINISTRATOR

Milwaukee, WI

Full-time

Onsite

Senior Level

5+ years exp

Bear Real Estate Group is seeking a highly skilled and strategic Senior Systems Administrator / Engineer to lead and manage the IT infrastructure, cybersecurity posture, and technical alignment for our family of companies. This role combines hands-on systems administration with team leadership and strategic oversight, ensuring effective technology support while driving IT strategy and security.

ConstructionProperty ManagementReal Estate

Responsibilities

Develop and maintain a comprehensive IT strategic plan including security, risk analysis, and technical alignment planning

Collaborate with leadership to align IT initiatives with business objectives, including budgeting, project planning, and technology roadmaps

Conduct quarterly strategic meetings to review technical risk, cybersecurity, and business continuity impacts

Lead, mentor, and manage the internal IT Team (both User and System support staff), including workload delegation, performance management, and professional development

Foster a culture of responsiveness and accountability in IT service delivery

Monitor and maintain network infrastructure (switches, firewalls, wireless systems) for uptime and reliability

Oversee antivirus protection (Bitdefender) and email filtering (Proofpoint) to mitigate threats

Implement security protocols, conduct risk assessments, and ensure compliance with best practices

Manage and maintain PC, server, and cloud environments to ensure optimal performance and reliability

Administer domain services, Active Directory, and DNS hosting

Manage Microsoft 365 environment including user management, licensing, and security configurations

Ensure all employees’ IT needs are consistently met through timely resolution of help desk tickets

Monitor help desk metrics to identify trends and implement process improvements

Develop and deliver employee IT training sessions (cybersecurity awareness, software tools, onboarding for new technology)

Oversee setup, maintenance, and upgrades of conference room A/V systems, video conferencing platforms, and collaboration tools

Ensure reliable, user-friendly meeting room technology is available for all staff

Oversee inventory of all company IT equipment, including computers, servers, networking devices, and peripherals

Monitor equipment performance, warranty status, and useful life

Make recommendations for repair, replacement, and upgrades based on lifecycle and business needs

Develop and enforce standards for hardware and software procurement to ensure consistency and cost-effectiveness

Direct accurate documentation of systems, configurations, and procedures

Provide regular reports on system health, help desk performance, and IT project progress

Qualification

IT strategyCybersecurityNetwork infrastructureTeam leadershipWindows ServerActive DirectoryMicrosoft 365Security toolsITIL FoundationCompTIA Security+CCNA/CCNPMicrosoft Azure Administrator AssociateCommunication skillsInterpersonal skillsLeadership skills