IT Help Desk Technician: Windows & Microsoft 365 Support

Jobtailor; Mentor (OH); On-site; USD 42,000 - 60,000; Full time

Job summary

Jobtailor is seeking an entry-level IT Help Desk Specialist in Mentor, Ohio. You will serve as the front line for end users, resolving Windows and Microsoft 365 issues while guiding users through procedures and best practices.

You will also image and deploy workstations, manage accounts in Entra ID/AD, and support onboarding/offboarding, inventory, and AV setup. A customer-focused, patient, and proactive learner attitude is essential.

Qualifications

• 1–2 years of help desk, customer service, or IT support experience
• Basic understanding of Windows 10/11 and Microsoft 365 applications
• Familiarity with common desktop hardware, printers, and peripherals
• Strong customer-service orientation with clear written and verbal communication skills
• Ability to follow documented procedures and escalate issues appropriately
• High school diploma or equivalent experience
• Industry certifications or coursework such as CompTIA A+, MS-900, or AZ-900, or active pursuit of these credentials
• Experience with ITSM or ticketing platforms such as ServiceNow, Atera, Freshservice, or similar tools
• Familiarity with Entra ID (Azure AD) and Active Directory fundamentals
• Experience supporting remote and hybrid users
• Prior IT internship, technical lab, or home-lab experience
• Friendly, patient, customer-focused attitude
• Eagerness to learn and develop technical skills
• Strong organizational skills and consistent follow-through
• Ability to explain technical steps in clear, plain language
• Dependable team player

Responsibilities

• Serve as the first point of contact for end users through phone, email, chat, and walk-up requests
• Troubleshoot and resolve common Windows desktop, laptop, printer, and peripheral issues
• Provide first-line support for Microsoft 365 applications, including Outlook, Teams, SharePoint, and OneDrive
• Assist with workstation setup, software installation, and device configuration
• Escalate unresolved or complex issues to Tier 2 with detailed troubleshooting notes
• Perform password resets and assist with MFA enrollment and sign-in issues
• Process account, group, and license requests in Entra ID and Active Directory
• Support onboarding and offboarding activities, including equipment setup and account activation
• Assist users with shared drives, distribution lists, and mailboxes
• Log, categorize, and track support requests in the ITSM platform
• Follow standard operating procedures and knowledge base articles
• Keep users informed of ticket status and expected resolution timelines
• Document troubleshooting steps and contribute to the knowledge base
• Prepare, image, and deploy workstations and peripherals
• Track hardware assets and assist with inventory and stock management
• Support conference room AV setup and basic connectivity issues

Skills

Customer service orientation

Clear communication

Organizational skills

Team player

Eagerness to learn

Education

High school diploma or equivalent

CompTIA A+

MS-900

AZ-900

Tools

ServiceNow

Atera

Freshservice

ITSM Platforms

Microsoft Teams

Outlook

SharePoint

OneDrive

Job description

Jobtailor is seeking an entry-level IT Help Desk Specialist in Mentor, Ohio. You will serve as the front line for end users, resolving Windows and Microsoft 365 issues while guiding users through procedures and best practices.

You will also image and deploy workstations, manage accounts in Entra ID/AD, and support onboarding/offboarding, inventory, and AV setup. A customer-focused, patient, and proactive learner attitude is essential.