Senior Desktop Technician – Executive Support

University of Massachusetts Medical School•Worcester, MA

About The Position

The Senior Desktop Technician – Executive Support is responsible for delivering white-glove IT services to the Chancellor, senior leadership, and their administrative teams within a fast-paced academic medical environment. This role requires a highly skilled, customer-focused technician with deep experience supporting macOS (primary) and Windows platforms, coupled with exceptional communication and relationship management skills. The position serves as a single point of accountability for executive IT issues, driving rapid triage, coordination, and resolution across infrastructure, applications, security, and other IT service teams. The ideal candidate demonstrates discretion, professionalism, and the ability to operate seamlessly in high-visibility, high-impact situations. A strong understanding of the academic and research environment is essential, including sensitivity to faculty workflows, administrative operations, and institutional priorities.

Requirements

5+ years of desktop support experience, including significant VIP/executive support.
Strong expertise in macOS support (Jamf or similar tools preferred).
Experience supporting both Mac and Windows enterprise environments.
Proven ability to manage high-pressure situations with professionalism and urgency.
Experience working in higher education or academic medical/research environments.

Nice To Haves

Exceptional customer service and interpersonal skills
Strong ownership mentality and accountability
Excellent verbal and written communication
High level of discretion and professionalism
Ability to navigate complex organizations and influence outcome

Responsibilities

Provide dedicated, high-touch IT support to the Chancellor, direct reports, and executive administrative staff.
Deliver proactive and reactive support with an emphasis on minimal disruption and rapid resolution.
Support primarily macOS-based environments, with additional support for Windows devices and enterprise applications
Ensure a consistent “white-glove” experience, including on-site, remote, and event-based support.
Serve as the primary owner for executive IT issues from intake through full resolution.
Drive end-to-end resolution by coordinating across IT teams (network, systems, security, AV, applications, etc.).
Escalate appropriately and follow through with urgency, ensuring timely updates and closure.
Operate with a “seconds to triage, minutes to action” mindset aligned with executive service expectations.
Partner closely with internal IT teams and external vendors to resolve complex technical issues.
Translate technical issues into clear, concise updates for executive stakeholders.
Advocate for executive needs within IT to ensure prioritization and accountability.
Manage and support macOS systems (primary), including device configuration, troubleshooting, and performance optimization.
Support Windows systems and standard enterprise applications (Microsoft 365, collaboration tools, etc.).
Assist with mobile devices, conferencing solutions, and executive office technology setups.
Support conference rooms, executive briefings, and high-profile meetings/events as needed.
Deliver impeccable customer service through clear, professional, and proactive communication.
Build trusted relationships with executive stakeholders and their support staff.
Maintain discretion and confidentiality in all interactions involving sensitive information.
Demonstrate understanding of the academic medical environment, including faculty, research, and administrative workflows.
Support unique use cases tied to academic leadership, governance, and institutional operations.
Adapt support approaches to align with academic calendars, events, and priorities.
Identify recurring issues and partner with IT teams to implement sustainable solutions.
Contribute to knowledge base documentation and process improvements.
Recommend enhancements to executive support models, tools, and service delivery.