SENIOR IT SYSTEM ADMINISTRATOR

Bear Real Estate Group; Kenosha (WI); On-site; USD 80,000 - 100,000; Full time

Job summary

A local real estate company in Kenosha is seeking a Senior IT System Administrator to lead its IT infrastructure and cybersecurity efforts. The ideal candidate will have over 5 years of experience in systems administration, a Bachelor's degree in Computer Science, and strong leadership skills. Responsibilities include managing IT staff, ensuring cybersecurity, and overseeing network performance. This full-time position offers a dynamic work environment with opportunities for professional development.

Qualifications

• 5+ years of experience in systems administration or engineering.
• Strong knowledge of Active Directory and DNS hosting.
• Preferred certifications include Microsoft Azure Administrator Associate, CompTIA Security+, ITIL Foundation, CCNA/CCNP.

Responsibilities

• Develop and maintain IT strategic plan including security and risk analysis.
• Monitor and maintain network infrastructure for uptime and reliability.
• Manage and maintain PC, server, and cloud environments.

Skills

IT strategy

Team leadership

Communication

Network infrastructure

Security tools

Cloud platforms

Education

Bachelor's degree in Computer Science or related field

Tools

Bitdefender

Proofpoint

Microsoft 365

Windows Server

Job description

Join to apply for the SENIOR IT SYSTEM ADMINISTRATOR role at Bear Real Estate Group

We are seeking a highly skilled and strategic Senior Systems Administrator / Engineer to lead and manage our IT infrastructure, cybersecurity posture, and technical alignment. This role combines hands‑on systems administration with team leadership and strategic oversight. The Senior Systems Administrator will manage our IT staff, ensuring that day‑to‑day technology support is delivered effectively while also driving higher‑level IT strategy, security, and long‑term planning.

Duties and Responsibilities

Strategic Leadership & Planning

• 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.

Network & Security Management

• 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.

Systems Administration

• 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.

Employee & End‑User Support

• 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).

Workplace 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.

IT Asset & Lifecycle Management

• 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.

Documentation & Reporting

• Direct accurate documentation of systems, configurations, and procedures.
• Provide regular reports on system health, help desk performance, and IT project progress.

Qualifications

• Bachelor’s degree in Computer Science, Information Technology, or related field (or equivalent experience).
• 5+ years of experience in systems administration or engineering.
• Proven experience in IT strategy, security, and team leadership.
• Strong knowledge of network infrastructure, Windows Server, Active Directory, and Microsoft 365.
• Experience with security tools (Bitdefender, Proofpoint) and cloud platforms.
• Excellent communication, leadership, and interpersonal skills.
• Preferred Certifications: Microsoft Azure Administrator Associate (or equivalent), CompTIA Security+, ITIL Foundation, CCNA/CCNP (a plus)

The above is intended to describe the general content of and requirements for the performance of this job. It is not to be construed as an exhaustive statement of duties, responsibilities, or physical requirements. Nothing in this job description restricts management’s right to assign or reassign duties and responsibilities to this job at any time.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Bear Real Estate Group is proud to be an Equal Employment Opportunity and affirmative action employer. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, disability, or other protected characteristics.

Seniority level

Mid‑Senior level

Employment type

Full‑time

Job function

Information Technology