Job DescriptionJob Description
We are seeking a highly experienced Sr. IT Systems Engineer to serve as a senior technical resource in a fast-paced, high-profile environment. This role will provide expert-level support for desktops, systems, networking, cybersecurity, and infrastructure. You will drive the resolution of complex business-critical issues while acting as a technical lead and trusted advisor to clients.
The ideal candidate will have deep technical expertise in Windows Server operating systems, including installation, configuration, performance tuning, role-based services (such as DNS, DHCP, AD DS, File Services), and advanced troubleshooting. You must be able to manage and recover from server-related failures in live production environments, as well as guide infrastructure improvement projects.
Our ideal candidate is a polished and professional engineer who can communicate effectively with executive stakeholders while delivering high-value technical outcomes across modern IT environments.
Key Responsibilities:
- Serve as the primary escalation point for all high-complexity technical issues across end-user systems, networking, and application environments.
- Provide expert-level support for Windows desktop OS, Microsoft 365, and related productivity tools.
- Install, configure, and maintain Windows Server environments (2016, 2019, 2022) including domain controllers, file servers, print servers, and other core infrastructure services.
- Perform root cause analysis and remediation of Windows Server issues affecting availability, performance, or security.
- Support and administer platforms including Active Directory, Azure AD, and Single Sign-On (SSO) integrations.
- Perform advanced troubleshooting of LAN/WAN networking, VPN connectivity, DNS/DHCP, and wireless infrastructure.
- Manage endpoint security, EDR platforms, vulnerability remediation, and compliance best practices.
- Lead technical implementations for client-specific solutions, including rollouts, upgrades, and migrations.
- Own and manage documentation, asset tracking, ticket resolution, and knowledge base updates.
- Collaborate with MSP engineering teams and third-party vendors to resolve infrastructure or service-related escalations.
- Deliver white-glove support to VIP and executive users, ensuring minimal disruption and maximum discretion.
- Identify recurring issues and recommend/implement proactive solutions to improve the end-user experience and reduce support demand.
- Expertise working with tools like FortiGate, Palo Alto, Azure, AWS, and the Microsoft ecosystem.
- Advanced networking expertise and the ability to understand and design complex IT architectures.
Required Qualifications:
- 10+ years of IT support experience, with 5+ years in a senior or Level 3 technical role.
- Expert-level experience with Windows Server installation, configuration, patching, and role management.
- Proficient in advanced troubleshooting of server-related issues including hardware, software, Active Directory replication, DNS, and Group Policy management.
- Expertise in Windows 10/11, Microsoft 365 (Outlook, Teams, SharePoint, OneDrive), and mobile device management (iOS, Android).
- Deep knowledge of Active Directory, Azure AD, Exchange Online, and Group Policy.
- Advanced understanding of networking protocols (TCP/IP, DNS, DHCP), VPNs, VLANs, and firewall configurations.
- Hands-on experience with security tools such as EDR, MFA, email security gateways, and compliance frameworks.
- Strong scripting or automation skills in PowerShell or equivalent.
- Familiarity with virtualization technologies (e.g., VMware, Hyper-V) and cloud computing fundamentals.
- Excellent communication skills, with proven success in supporting C-level and high-sensitivity users.
- Proficient in ITSM platforms (e.g., ServiceNow, HaloPSA, ConnectWise) and RMM/monitoring tools.
- Ability to work independently and own outcomes from troubleshooting to resolution.
- Industry certifications such as Microsoft 365 Certified: Enterprise Administrator Expert, CompTIA Security+, Cisco CCNA, or equivalent are strongly .
- : Microsoft Certified: Windows Server Hybrid Administrator Associate or similar.
Desired Qualifications:
- Prior experience supporting VIP users in legal, financial, media, or other executive-heavy industries.
- Familiarity with ITIL practices and process-oriented service delivery.
- Experience with MDM tools (Intune, Jamf) and endpoint management policies.
- Exposure to AV/conference room systems, Zoom Rooms, or Microsoft Teams Rooms.
- Strong analytical thinking and the ability to identify and mitigate systemic issues.
- Track record of mentoring junior techs and improving team performance.
- Project management experience or exposure to formal project workflows (Agile, PMP, etc.).