Windows & Microsoft 365 Administrator (Hybrid)

Shape the Future of a Modern Hybrid Infrastructure at OCB!

Are you a skilled IT professional with deep expertise in Windows Server, Microsoft 365, and virtualization technologies? Do you thrive in environments where you can own systems end-to-end, implement smart automation, and strengthen security across on-prem and cloud platforms? If so, we want to meet you.

OCB is seeking an experienced Windows & Microsoft 365 Administrator to support, maintain, and enhance our hybrid IT environment. This is a hands-on technical role ideal for someone who loves solving complex problems, optimizing systems, and driving operational excellence.

This position will be Monday Through Friday 8-4:30 with the option of up to 2 days hybrid.

What You’ll Do

As a key member of our infrastructure team, you will:

• Manage and support Windows Server environments (2016/2019/2022/2025) including Active Directory, DNS, DHCP, and GPOs

• Administer core Microsoft 365 services such as Exchange Online, Teams, SharePoint, OneDrive, Azure AD, and Intune

• Support and maintain VMware infrastructure, including ESXi hosts and vCenter

• Monitor system performance, reliability, and availability across both on-prem and cloud ecosystems

• Perform regular updates, patching, and backups—ensuring compliance with security policies

• Use PowerShell to automate routine processes and improve efficiency

• Partner with cross-functional teams to deliver infrastructure upgrades and strategic projects

• Maintain detailed documentation of systems, procedures, and configurations

• Leverage M365 Security & Compliance tools (DLP, Conditional Access, Defender) to strengthen enterprise security posture

What You Bring

• 5–8 years of hands-on experience with Windows Server & Microsoft 365 administration

• Strong proficiency with Azure AD and the Microsoft 365 Admin Center

• Solid experience with VMware vSphere, ESXi, and vCenter

• Expertise in AD, Group Policy, DNS, DHCP, and related infrastructure services

• Working knowledge of security best practices for both cloud and on-prem environments

• Strong PowerShell scripting skills

• Excellent troubleshooting abilities and clear communication skills

Preferred Skills & Certifications

• Experience with M365 security frameworks including Compliance Center, Threat Management, and Secure Score

• One or more of the following certifications:

  • Microsoft 365 Certified: Modern Desktop Administrator Associate

  • Microsoft Certified: Security Administrator Associate

  • VMware Certified Professional (VCP) or equivalent

Education

• Bachelor’s degree in Computer Science, Information Technology, or related field
  —or equivalent hands-on experience

Benefits Offered:

• Health & Dental Insurance- eligible 1st day of employment
• Paid time off and paid holidays
• Health & Dependent Reimbursement Accounts
• 401(k) Plan with company contribution
• Company paid Life and LTD Insurance
• Employee discounts

To find out more about OCB, please visit our website at www.eyeboston.com. OCB is an Equal Opportunity Employer.