Windows and Microsoft 365 Administrator — Plymouth, MA

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.

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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

· Microsoft 365 administration: Demonstrated experience managing Entra ID, Exchange Online, SharePoint Online, Teams, and Intune in a production environment.

· Identity security: Ability to implement Conditional Access, phishing-resistant MFA, privileged identity management, emergency access accounts, and restrictions on unmanaged devices.

· PowerShell and Microsoft Graph automation: Ability to automate onboarding, offboarding, license management, access reviews, and configuration reporting.

· Microsoft Copilot administration and governance: Hands-on experience deploying and managing Microsoft 365 Copilot, including licensing, permissions, data protection, agent controls, and third-party integrations.

· Application governance: Experience reviewing enterprise applications, OAuth permissions, service principals, and administrative consent to identify and restrict excessive access.

· Data protection and external sharing: Ability to manage sensitivity labels, DLP policies, retention controls, external sharing, and guest access across Microsoft 365.

· Troubleshooting and investigations: Ability to investigate issues using Entra sign-in logs, audit logs, message tracing, and endpoint compliance data, and support security incident response.

· Controlled, documented administration: Commitment to least-privilege access, configuration documentation, change management, and validation before broad deployment.

· Licensing and recovery: Ability to optimize licensing costs and validate recovery procedures for users, mailboxes, and business data, with an understanding of native retention and backup limitations.

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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

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Preferred Skills & Certifications

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

· One or more of the following certifications:

o Microsoft 365 Certified: Modern Desktop Administrator Associate

o Microsoft Certified: Security Administrator Associate

o VMware Certified Professional (VCP) or equivalent

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Education

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

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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 ••••••••