IT Project Specialist and Implementer

Technical Support International•Town of Summit, WI

19d•$84,000 - $100,000•Hybrid

About The Position

Technical Support International (TSI), based in Foxboro, MA, is a provider of outsourced IT and cybersecurity services for small and medium-sized businesses throughout New England. TSI delivers remote support, field support, managed services, security services (MSP/MSSP), and project management to our clients. The Project Specialist is primarily responsible for implementing IT projects for TSI’s clients. Working closely with TSI Project Managers, this role focuses on executing project plans, deploying solutions, and ensuring technical deliverables are completed on time and to client expectations. Project work includes deployments, upgrades, migrations, security initiatives, and other client-focused implementations. In addition to project responsibilities, this role provides occasional field support during client emergencies or periods when project demand is lower. The role requires light, localized travel to client sites, with flexibility in scheduling.

Requirements

CCNA or CCNP certifications preferred (or equivalent experience).
Knowledge of current networking technologies.
Strong experience with Windows 10/11 and Windows Server 2016/2019/2022/2025.
Knowledge of Microsoft Office and Microsoft 365 administration.
Proficiency with TCP/IP, DNS, DHCP, and Active Directory.
Understanding of LAN/WAN, firewalls, routers, and VPN/remote access solutions.
Experience with IT security practices strongly preferred.
Bachelor’s degree strongly preferred; or equivalent education plus experience.
Minimum 4–6 years’ experience in IT support services.
Direct client-facing IT support experience required.
Must have a valid driver’s license and use of a personal vehicle for work (mileage reimbursement provided).

Nice To Haves

Experience installing and configuring Windows Servers a plus.
Microsoft Intune experience a plus.
macOS and Linux experience a plus.
Cloud certifications (Microsoft 365, Azure, AWS) a plus.
Microsoft certifications (current Microsoft 365 or Azure) a plus.

Responsibilities

Execute IT projects as developed and scoped by TSI Project Managers.
Implement technical solutions such as system upgrades, network deployments, cloud migrations, and security initiatives.
Collaborate with Project Managers to understand project requirements, deliverables, and client expectations.
Provide timely updates to Project Managers on progress, risks, and technical challenges.
Ensure project documentation is completed accurately and maintained in ConnectWise PSA.
Provide onsite technical assistance during client emergencies or when not engaged in project work.
Respond to urgent customer requests in a timely and professional manner.
Install, configure, and repair computer systems, networks, and peripherals when required.
Troubleshoot and resolve issues with LAN/WAN environments.
Perform malware removal, endpoint security hardening, and patch management as necessary.
Assist other field engineers at client sites as needed.
Use TSI’s specialized tools (including ConnectWise Automate, PSA) to diagnose, resolve, and document technical issues.
Maintain up-to-date technical knowledge and meet training goals set by management.
Take ownership of technical issues through resolution; escalate to senior resources when necessary.
Partner with TSI Project Managers to implement projects according to defined scope, timeline, and deliverables.
Provide technical input on resource requirements, risks, and dependencies during project execution.
Maintain strong communication with internal teams and clients throughout the project lifecycle.
Assist with additional duties as requested.
Adhere to all company policies and standards of conduct, including safety and workplace harassment policies.
Participate in on-call rotation for after-hours support.