Windows Administrator

Gelbergroup; Chicago (IL); On-site; USD 75,000 - 95,000; Full time

Benefits offered by this job

401(k) retirement program with employer match

Comprehensive health benefits

Tuition reimbursement

Flexible Spending Accounts

Life insurance

Health club membership

Generous vacation time

Weekly catered lunches

Social events

Casual dress code

Job summary

Gelbergroup is looking for a Windows Administrator to join their infrastructure team in Chicago. This role offers a fantastic opportunity for someone early in their IT career to gain hands-on experience in a dynamic trading environment, benefiting from strong mentorship and long-term growth potential.

The position requires onsite presence with potential eligibility for a hybrid schedule after onboarding. Responsibilities include deploying and configuring Windows environments, managing Active Directory, and troubleshooting various IT issues.

Benefits include comprehensive health coverage, a 401(k) plan, generous vacation time, and a supportive work culture with various social activities.

Qualifications

• 3+ years of experience in Windows Administration or similar role.
• Experience with on-premises Active Directory (AD) design and management.
• Knowledge of DNS management.
• Understanding of DHCP/basic networking fundamentals.

Responsibilities

• Deploy, configure, and support Microsoft Windows desktops and servers.
• Install software, troubleshoot issues, and manage printers.
• Administer and support a Windows on-premises domain environment.
• Document procedures and contribute to process improvements.

Skills

Windows Administration

Active Directory

DNS management

Networking fundamentals

Troubleshooting skills

Education

Bachelor’s degree

Tools

WDS/MDT imaging tools

Azure

O365

Job description

Gelber Group is seeking a Windows Administrator to join our infrastructure team. This is an excellent opportunity for someone early in their IT career who wants hands‑on experience in a fast‑paced, performance‑driven trading environment with strong mentorship and long‑term growth potential.

Position requires full‑time onsite presence in our Chicago office, with eligibility for a 4‑day/week hybrid schedule after onboarding is complete.

What you’ll do:

• Deploy, configure, and support Microsoft Windows desktops and servers
• Install software, manage printers/peripherals, and troubleshoot hardware and software issues
• Administer and support a Windows on‑premises domain environment, including:
• Active Directory design and management
• Group Policy Objects (GPOs)
• DNS management
• Manage CIFS shares and NTFS/share‑level permissions
• Support cloud services including Azure Active Directory, Intune, and Office 365
• Build and maintain deployment images using Windows Deployment Services (WDS) and Microsoft Deployment Toolkit (MDT)
• Apply basic networking knowledge including DHCP
• Collaborate across Infrastructure, Security, Networking, and Trading teams
• Document procedures and contribute to process improvements

Role requirements:

• Bachelor’s degree
• 3+ years of experience in Windows Administration or similar role
• Experience with on‑premises Active Directory (AD) design and management
• Knowledge of DNS management
• Understanding of DHCP/basic networking fundamentals

What we’d like to see:

• Experience with WDS/MDT imaging tools
• Strong critical thinking and troubleshooting skills
• Clear communication skills and strong work ethic
• Ability to prioritize and operate with urgency in a fast‑paced environment
• Ability to lift/move equipment up to 50 lbs.
• Experience with the following technologies encouraged:
  • OpenAI/ChatGPT Enterprise
  • Slack
  • Office 365 (O365)
  • Azure
  • Intune
  • Mimecast
  • Absolute
  • Zscaler
  • Proxmox

Benefits Highlights

• Traditional and Roth 401(k) retirement program with discretionary employer match
• Comprehensive health benefits including medical coverage provided by Blue Cross and Blue Shield (PPO and HDHP/HSA) and dental coverage; generous employer cost‑sharing
• Tuition reimbursement for Undergraduate and Graduate courses
• Flexible Spending Accounts for health care and dependent care; pre‑tax commuter benefits for parking and transit expenses
• Life insurance and long‑term disability coverage
• Health club membership with on‑site facilities (and reciprocal memberships)
• Generous vacation time (23‑day accrual in first full calendar year of employment; prorated accrual in initial year), paid holidays, and paid maternity/paternity leave
• Weekly catered lunches and monthly continental breakfasts
• Social events including sponsored 5k races and annual company party
• Enjoyable work environment including golf simulator
• Employee referral bonus program
• Charitable giving and company matching opportunities
• Casual, relaxed dress code

The approximate annual base compensation range for this position in Chicago, IL is $75,000 to $95,000. The actual offer, reflecting the total compensation package plus benefits, will be determined by a number of factors which include but are not limited to the applicant’s experience, knowledge, skills, and abilities; geographic location; and internal equity. In addition to your salary, our total rewards package includes health benefits, a 401(k) plan, PTO, parental leave, professional development, tuition reimbursement and discretionary bonus, enhancing your overall total rewards package.