Sr. Technical Support Specialist

Role: Sr. Technical Support Specialist - Employee Tech Services (Windows)

Location: Windsor, CT  (Onsite – 5 Days/Week) -  Need locals only

Interview Mode: In person also

Make sure candidate have strong exp. with executive support and white glove

Position Summary:

We are seeking a highly skilled and customer-focused Lead Solutions Engineer to join our Employee Tech Services team. This role is pivotal in delivering white-glove, deskside IT support to executives and staff in a fast-paced financial services environment. You will lead the resolution of complex technical issues, drive operational excellence, and ensure seamless end-user experiences across hardware, software, mobile, and AV systems.

Key Responsibilities

·         Provide Level 1 and 2+ deskside and remote troubleshooting support for Windows-based environments, including desktops, laptops, mobile devices, and AV/conferencing systems.

·         Troubleshoot and resolve issues related to hardware, software, network, and user credentials.

·         Coordinate and execute office moves, tech refreshes, infrastructure buildouts, and perform onsite installations.

·         Maintain and update tickets in alignment with SLA and KPI targets.

·         Deliver executive-level white-glove support, ensuring high-touch service and discretion.

·         Lead the deployment of software releases, patches, and system upgrades across end-user devices.

·         Manage IT asset lifecycle including procurement, inventory, and disposal.

·         Collaborate with cross-functional IT teams and provide mentorship to junior engineers.

·         Participate in incident response (P1–P5) and root cause analysis.

·         Support change, release, and problem management processes.

·         Experience in Microsoft services including Active Directory, DNS, DHCP, Microsoft 365, Print Server management, and Group Policies (GPOs).

·         Proficient in Microsoft Windows OS (Windows 10, Windows Server 2019), Virtual Desktop Infrastructure, and workstation imaging.

·         Competent in Microsoft Office 365 and Azure administration.

·         Administer security tools such as Putty, FTP, Antivirus, and Robocopy.

·         Deploy patches and system-related software.

·         Manage workflow and follow up on helpdesk issues via ticketing systems.

·         Implement systems-related work through full lifecycle, coordinating with teams and vendors.

·         Monitor systems and evaluate performance and latency concerns.

·         Troubleshoot servers, applications, PCs, and network-related equipment.

·         Document processes, application instructions, and IT-related topics.

Required Qualifications:

·         Bachelor’s degree or 5–8 years of relevant IT experience.

·         Proven experience supporting Windows OS, Microsoft 365, Active Directory, and enterprise collaboration tools.

·         Strong knowledge of ITIL processes: Incident, Problem, Change, and Release Management.

·         Experience with IT Asset Management (ITAM) tools and practices.

·         Excellent communication, interpersonal, and problem-solving skills.

·         Ability to manage multiple priorities in a high-pressure environment.

·         Willingness to work flexible hours, including evenings and weekends, as needed.

·         Occasional travel to our Braintree, MA location (20 min. away) for onsite support

Preferred Skills & Certifications:

·         Industry certifications (e.g., Microsoft, ITIL, CompTIA).

·         Experience in a financial services or managed services environment.

·         Familiarity with performance management, capacity planning, and business relationship management.

·         Proficiency in using scripting to automate tasks.