Company Information 

At Bit By Bit, we’ve been helping organizations thrive since 1987. Originally founded as a database application development and networking company, we’ve grown into a full-service IT firm and a recognized leader in delivering reliable, cost-effective managed IT services across the Tri-State area. 

Our team specializes in building and managing solutions that solve critical business challenges. With a unique blend of business technology expertise, certified technicians, and proven processes, we provide our clients with tailored IT solutions that improve productivity, strengthen security, streamline communications, and reduce costs. Beyond technology, our culture is rooted in humility and curiosity, and our vision is simple: to help untangle people and process challenges so businesses can move forward with confidence. 

Role Summary 

We are seeking an experienced Senior Windows Systems Engineer / Administrator to support and administer enterprise Microsoft infrastructure across Windows Server, Microsoft 365, Active Directory, Azure, and virtualized environments. 

This is a senior technical role responsible for the ongoing administration, maintenance, troubleshooting, lifecycle management, and improvement of critical server and cloud infrastructure. The successful candidate will have extensive hands-on experience managing Microsoft environments and will be comfortable working independently on complex technical issues while collaborating with other engineers, administrators, and stakeholders. 

The role also requires the ability to provide technical guidance and coordinate the work of a small team of highly technical engineers and administrators when needed. 

Requirements

Duties and Responsibilities 

Windows Server Administration 

• Administer, maintain, and support Windows Server environments, including Windows Server 2012 R2, 2016, 2019, 2022, and 2025. 

• Manage the full Windows Server operating system lifecycle, including installation, configuration, upgrades, patching, performance tuning, troubleshooting, and decommissioning. 

• Support both physical and virtual Windows Server environments. 

• Monitor server health, performance, capacity, and availability and proactively address infrastructure issues. 

• Troubleshoot complex Windows Server incidents and identify appropriate corrective and preventative actions. 

• Plan and execute server upgrades, migrations, maintenance, and infrastructure changes. 

Active Directory & Core Microsoft Infrastructure 

• Administer and support enterprise Active Directory environments, including Microsoft Entra ID (Azure Active Directory). 

• Manage users, groups, permissions, organizational units, authentication, and other Active Directory services. 

• Administer and troubleshoot Group Policy (GPO), DNS, DHCP, Windows File Systems, and Print Servers. 

• Support hybrid identity environments and integration between on-premises Active Directory and Microsoft cloud services. 

• Troubleshoot authentication, access, replication, policy, and other Active Directory-related issues. 

Microsoft 365 & Exchange 

• Administer and support Microsoft 365 environments. 

• Manage Microsoft Exchange and Exchange Online administration, configuration, troubleshooting, and maintenance. 

• Support Microsoft 365 users, licensing, permissions, mailboxes, groups, and related services. 

• Troubleshoot complex Microsoft 365 and Exchange issues and coordinate resolution of service-impacting incidents. 

• Support Microsoft 365 and Exchange migrations, upgrades, and configuration changes as required. 

Microsoft Azure 

• Administer and support Microsoft Azure environments. 

• Manage Azure-based infrastructure and services related to Windows Server and Microsoft enterprise environments. 

• Support identity, access, security, configuration, and integration between Azure and on-premises systems. 

• Troubleshoot Azure infrastructure and connectivity issues. 

Virtualization 

• Administer Windows Server nodes within virtualized environments. 

• Manage and support Microsoft Hyper-V environments. 

• Support VMware environments as required. 

• Assist with or lead migrations from VMware to Microsoft Hyper-V where applicable. 

• Troubleshoot virtual machine, host, storage, resource, and performance-related issues. 

Additional Systems Administration 

• Configure, administer, and troubleshoot Microsoft IIS. 

• Configure and administer SFTP environments and services. 

• Support Windows file systems, permissions, storage, and related infrastructure. 

• Participate in infrastructure upgrades, migrations, deployments, and technical projects. 

• Apply security, patching, and system-management standards across supported infrastructure. 

Technical Leadership & Service Delivery 

• Provide senior-level technical support and guidance for complex infrastructure issues. 

• Assist and mentor engineers and administrators in troubleshooting and systems administration. 

• Coordinate technical activities across a small team when required. 

• Prioritize competing incidents, service requests, maintenance activities, and project requirements. 

• Work collaboratively with technical teams and other stakeholders to resolve infrastructure issues. 

• Maintain accurate technical documentation, system configurations, procedures, and change records. 

• Follow established change-management, security, and operational procedures. 

• Use ServiceNow or other service-management platforms to manage incidents, requests, changes, and technical work. 

Qualifications 

Required Experience & Technical Skills 

• Minimum of 10 years of hands-on experience supporting Windows Server environments, including operating system installation, configuration, performance tuning, patching, upgrades, troubleshooting, and decommissioning. 

• Advanced experience administering Windows Server environments across physical and virtual infrastructure. 

• Strong experience administering Active Directory and Microsoft Entra ID/Azure Active Directory. 

• Advanced Microsoft 365 and Exchange/Exchange Online administration experience. 

• Strong Microsoft Azure administration experience. 

• Hands-on experience with Group Policy (GPO), DNS, DHCP, Print Servers, and Windows File Systems. 

• Experience configuring and administering IIS. 

• Experience with SFTP setup and administration. 

• Strong virtualization experience, particularly Microsoft Hyper-V. 

• Experience administering VMware environments. 

• Strong troubleshooting, analytical, and problem-solving capabilities. 

• Demonstrated ability to manage complex technical issues through resolution. 

• Experience providing technical direction or coordinating the work of engineers and administrators. 

Professional Capabilities 

• Strong time-management, prioritization, and multitasking skills. 

• Ability to think critically, analytically, and strategically. 

• Ability to work independently and take ownership of complex technical problems. 

• Strong written and verbal communication skills. 

• Ability to communicate technical issues clearly to both technical and non-technical stakeholders. 

• Strong attention to documentation, security, operational standards, and change management. 

• Ability to collaborate effectively within a technical team and across functional areas. 

Education 

• Bachelor’s degree in Computer Science, Engineering, Information Technology, or a related technical field, or equivalent relevant professional experience. 

• Master’s degree in a relevant field is preferred. 

Preferred Qualifications 

• Experience working in a ServiceNow environment. 

• Experience migrating VMware infrastructure to Microsoft Hyper-V. 

• Experience supporting hybrid Microsoft environments combining on-premises infrastructure with Microsoft Azure and Microsoft 365. 

• Previous experience leading or managing a small team of highly technical engineers or systems administrators. 

• Relevant Microsoft, Azure, VMware, or other infrastructure certifications are considered an asset. 

Benefits

Compensation & Benefits 

• Base Pay: $75-$85/Hour 

• Benefits package includes: Medical, dental, paid vacation, and retirement plan 

Working Conditions 

• Location: Hybrid, in Central New Jersey 

• Schedule: Monday to Friday  

• Environment: Fast-paced MSP environment supporting client infrastructure and enterprise systems 

• Occasional after-hours responsibilities may be required