Technical Support Specialist - Level 2

Company: Shipshape IT LLC
Location: Bethesda
Posted on: April 3, 2026

Job Description:

Job Description Job Description Position: Technical Support Specialist – Level 2 Shipshape IT is seeking to grow its technical team to keep pace with its steady growth. Shipshape IT is a provider of fixed-price IT support to small and mid-size businesses in the DC metro area. The company is looking for highly motivated individuals with the ability to effectively communicate with both internal staff and clients. Candidates must also possess a strong information technology background and knowledge. Position Summary The Technical Support Specialist Level 2 (TSS L2) role within the Support Services group will be responsible for ensuring all client-facing customer support requests are resolved in a complete, correct, and timely manner. Typical responsibilities are: Tier 1 and 2 Issue Resolution – The TSS L2 should be capable of taking ownership and resolving issues directly or engaging the correct internal or external resources to drive the issue to resolution. The TSS L2 will also assist with certain escalated issues. Responding to Networking/Server Alerts – At time, the TSS L2 will be responsible for assisting with resolution of network and server related issues to ensure maximum uptime for all clients. Onsite Support – The TSS L2 will be required to make scheduled and unscheduled onsite visit to client offices and homes to assist with support items that cannot be addressed and resolved remotely. Documentation – Along with all other technical staff, the TSS L2 will participate in reviewing and maintaining documentation of clients’ information technology infrastructure and systems. The TSS L2 will also be responsible for accurately documenting their time and work completing on assigned tasks. Preferred Experience Background The ideal Technical Support Specialist will have tier 1 and 2 experience performing Windows and Mac desktop support in a business environment. Prior experience working in a desktop support role for an Information Technology Managed Services Provider (MSP) is beneficial, but not required. Our ideal team members will strive to provide a high level of customer service and possess exceptional verbal and written communication skills. This position will be highly collaborative with staff members of varying degrees of experience and technical expertise and will provide opportunities to learn new skills and to take on additional responsibilities. Team members will be most successful by employing critical thought and analysis to learn new technologies and consistently improve in customer service. Responsibilities All areas of responsibility listed below are essential to the satisfactory performance of this position. Any non-essential functions are assumed to be included in "other related organizational and logistical duties as may be reasonably assigned": - Respond to and resolve client incidents via remote and on-site desktop support. Incidents are submitted via phone calls and email. - Resolve client system outages and coordinate client communication. - Maintain ownership of multiple client issues and incidents while independently researching reliable and scalable solutions. - Facilitate hardware orders and deploy new workstations - Update client documentation and standard procedures - Maintain response SLAs and follow standard operating procedures for triage and troubleshooting. - Collaborate with other Support Services staff to ensure a positive and effective client experience. - Provide regular status updates to Support Service Manager and other senior staff. - Attend regular individual and team supervision meetings - Maintain top-level customer service and communications, both written and verbal, within Shipshape IT and with clients. - Participate in training and development of customer service and technical skills. - Participate in Shipshape IT on-call rotation Required Experience The position requires familiarity and fundamental skill levels with the following technologies: - Windows Desktop OS (installation, support, and basic troubleshooting) - Mac OS - Microsoft Office Applications (basic use, installation, and troubleshooting) - Windows Server OS - Windows Active Directory Administration - Microsoft 365 Management (Users, Teams, Exchange, OneDrive, SharePoint) - Microsoft Azure Administration - Managed antivirus/EDR solutions - Managed backup solutions - TCP/IP networks and network devices (routers, switches, firewalls) troubleshooting and configuration - Wireless Network Connectivity - DNS and SSL certificates - Apple and Android phones Education and Certifications Preferred, Not Required - Bachelor's degree in Computer Science or Information Systems, or other related disciplines - Certifications: CompTIA A, Network, Security, MCSE, VMware Additionally Must Possess As Technical Support Specialist, you will interact extensively (both over the phone and in person) with end-users that possess a wide range of technical knowledge. As such, you will need to possess strong analytical skills, excellent interpersonal skills, ability to design workable solutions to problems in a timely manner, the ability to travel to client sites (local travel only) and a strong customer service ethic. You may be responsible for, and candidates should be able to perform light physical work. Examples would include things such as lifting, moving, and relocating computers or other information technology infrastructure within an office or data center facility. Job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee. Shipshape IT is an Equal Opportunity Employer.

Keywords: Shipshape IT LLC, Bel Air South , Technical Support Specialist - Level 2, IT / Software / Systems , Bethesda, Maryland