IT Operations Support Technician II (1099 Contract))

Position Summary

The IT Operations Technician II serves as a critical resource for end-user technology support across the company. This hands-on, on-site role is responsible for the day-to-day support of Windows and macOS devices, Microsoft 365 applications, multi-factor authentication tools, and enterprise IT systems. The ideal candidate brings strong technical aptitude, exceptional communication skills, and a service-first mindset — with demonstrated experience supporting executive leadership and operating effectively in a fast-paced, compliance-driven healthcare environment.

Key Responsibilities

End-User Technical Support

• Serve as the primary point of contact for Tier I-II technical support requests submitted via ticketing system, phone, email, and walk-up


• Diagnose and resolve hardware, software, and connectivity issues on Windows 10/11 and macOS devices


• Support Microsoft 365 applications including Outlook, Teams, SharePoint, OneDrive, Word, Excel, and PowerPoint


• Troubleshoot Microsoft Authenticator and multi-factor authentication (MFA) issues, including device registration and access recovery


• Administer and support environments via Microsoft Admin Center, including user account management, licensing, and group policies


• Troubleshoot macOS-specific application and system issues, including OS updates, permissions, connectivity, and software compatibility

Device Management & Imaging

• Perform laptop imaging, configuration, and deployment for new hires and device refresh cycles


• Maintain device inventory records and ensure accurate asset tracking across both organizations


• Manage device enrollment in MDM/endpoint management platforms (e.g., Intune/Endpoint Manager)


• Coordinate equipment staging, setup, and decommissioning in alignment with IT lifecycle policies

Executive & VIP Support

• Provide dedicated, high-priority technical support for C-suite and senior leadership with discretion and professionalism


• Proactively identify and resolve potential issues before they impact executive productivity


• Assist with AV/conferencing setup and troubleshooting for leadership meetings, presentations, and video calls


• Handle sensitive requests with confidentiality and a white-glove service approach

Customer Service & Communication

• Deliver outstanding customer service to all staff, maintaining a calm, patient, and solutions-oriented demeanor


• Communicate technical issues and resolutions clearly to non-technical users, both verbally and in writing


• Document all support activities, troubleshooting steps, and resolutions accurately in the IT ticketing system


• Follow up on open tickets to ensure timely resolution and end-user satisfaction

IT Operations & Collaboration

• Collaborate with the IT team on infrastructure projects, system upgrades, and security initiatives


• Support onboarding and offboarding processes including account provisioning, hardware setup, and access management


• Assist with HIPAA-compliant data handling practices and adherence to IT security policies


• Escalate complex or unresolved issues to Tier III or appropriate IT leadership with thorough documentation

Required Qualifications

• Associate's degree in Information Technology, Computer Science, or related field; or equivalent work experience.


• 2+ years of experience in a Tier I/II IT support or helpdesk role


• Proven hands-on experience supporting both Windows 10/11 and macOS environments


• Demonstrated experience supporting Microsoft 365 suite and Microsoft Admin Center


• Experience with laptop imaging and device deployment workflows


• Prior experience providing support to executive or senior leadership personnel


• Windows 10/11 — installation, configuration, troubleshooting, updates, and Group Policy

Preferred Qualifications

• Relevant certifications: CompTIA A+, Microsoft 365 Certified: Modern Desktop Administrator, or Apple Certified Support Professional (ACSP)

Work Environment & Physical Requirements

• Fast-paced, compliance-driven healthcare and specialty pharmacy environment where


• Adherence to HIPAA standards and IT security policies


• Exposure to sensitive business and patient-related information


• Collaborate with cross-functional teams and interact with staff at all levels of the organization, including C-suite leadership


• Ability to lift and carry IT equipment, including desktop computers, monitors, and peripherals, up to 50 pounds


• Prolonged periods of sitting, standing, and walking throughout the facility to provide on-site support


• Ability to bend, kneel, crouch, or crawl in confined spaces to access hardware, cabling, or equipment installations


• Frequent use of hands and fingers for typing, equipment handling, and fine motor tasks related to hardware setup and repair


• Ability to work at a computer workstation for extended periods with visual acuity sufficient for screen-based tasks


• Occasional climbing of ladders or step stools for AV or equipment mounting needs


• Ability to transport equipment between office locations or floors as needed