IT Systems Helpdesk Supervisor

Cayuse Holdings•Pendleton, OR

3d•$60,000 - $80,000•Onsite

About The Position

The IT Systems & Helpdesk Supervisor holds primary responsibility for overseeing the maintenance and implementation of IT systems and managing helpdesk tickets. This role includes handling all Tier IV escalations, which require administrative-level attention, and ensuring that all other tickets are resolved promptly and appropriately. The supervisor will directly oversee IT department personnel responsible for systems management and helpdesk support. Responsibilities include conducting regular performance evaluations for direct reports and approving their timesheets. Additionally, the IT Systems & Helpdesk Supervisor is tasked with planning, executing, and delivering new IT projects or initiatives related to systems and helpdesk operations. This role involves providing a final review of all helpdesk and systems-related reports and tasks on a weekly basis to the Director of IT. The supervisor will also participate in bi-weekly meetings with the Director of IT to discuss the progress of ongoing projects and employee performance. This position aligns with Cayuse’s core values of Innovation, Excellence, Collaboration, Adaptability, and Integrity by fostering technical solutions that meet customer needs, promoting teamwork, and prioritizing quality in deliverables.

Requirements

Certification with CompTIA and/or Microsoft.
One of the following certification stacks must be awarded within one year of hire date:
CompTIA A+, Network+, Security+
Microsoft 365 Certifications Path as defined by the Director of IT
At least 2 years of experience working in the following areas:
Microsoft Entra administration
Microsoft O365 Web App administration
Microsoft Server 2016 and higher
VMware VSphere architecture
Linux OS (Debian/RHEL) and administration
Windows
PowerShell and Batch scripts
MS Active Directory administration
Microsoft O3656 and Entra admin tools
Secret Clearance is required.
Must be able to pass a background check.
May require additional background checks as required by projects and/or clients at any time during employment.
Minimum Skills:
Exceptional interpersonal skills with the ability to communicate in a clear, professional, and articulate manner.
Exceptional verbal and written communication skills.
Excellent organizational, analytical, and problem-solving skills with high-level attention to detail.
Proven ability to multitask and prioritize in a fast past environment with changing priorities; adaptable to change and a quick learner.
Must be self-motivated and able to work well independently as well as on a multi-functional team.
Ability to handle sensitive and confidential information appropriately
Proficient in MS Office, Word, Outlook, PowerPoint, and Excel.
A cooperative mindset and a strong commitment to working with others, exemplified by a service-oriented approach.
Proficiency in collaborating with and providing clear, effective instruction to individuals in technical support roles.

Nice To Haves

Associate or bachelor’s degree in an IT-related field.

Responsibilities

Supervises All IT Systems
Ensures that all systems are monitored to ensure security and availability to specific users.
Analyze, isolate, resolve and provide prevention measures for all systems-related IT issues.
Ensure that the design of each system will allow all components to work properly together.
Create and maintain systems integrations where appropriate.
Maintain systems efficiency.
Coordinate and work with 3rd party vendors to meet business objectives.
Maintain security updates.
Maintain all other updates/upgrades for systems.
Ensure stability/redundancy of all systems.
Maintain data thresholds.
Perform regular access audits.
Establish monitoring protocols and regular reporting as well as alerts.
Supports Cayuse security personnel to maintain systems redundancy and failover plans to support overall business continuity/disaster recovery.
Work with management to provide systems recommendations to support business growth and improve performance.
Act as the subject matter expert (SME) for all IT-related projects, systems and services.
Maintain an on-going repository of systems-related projects, project milestones/deadlines, and project state (open, closed, pending etc.).
Maintain all systems documentation and SOPs.
Supervise all helpdesk support
Ensure all helpdesk tickets are handled in a timely, professional manner.
Assist helpdesk employees where necessary, ensuring that helpdesk tickets are handled properly.
Act as Tier IV support for helpdesk tickets.
Asset management and tracking logs/repositories.
ZenDesk ticketing system administrative duties (adding/removing agents, adding/removing products(projects), administrating ticketing groups, etc.).
Ensure the IT work area is clean, organized, and free of unnecessary clutter.
Supervises the deployment of new workstations.
Supervises the reclaimation of IT equipment when employees are separated.
Supervises the shipping/receiving of IT materials.
Ensure the IT on-call and after-hours support is properly staffed.
Proper organization of all IT equipment in the IT workspace.
Act as a mentor for all junior level IT members.
Assist in training and onboarding new IT personnel.
Establish annual IT goals and initiatives with direct reports and ensure that deliverables are met in a timely manner.
Approve direct report timesheets.
Hold regular meetings with direct reports to review the progress of their goals and provide direction as needed.
Work with management to provide a realistic IT state of affairs and company direction/goals for future improvements and auditing practices.
Diagnose and address IT Systems and Helpdesk needs in cost effective ways.
Use standardized methods for troubleshooting systems to resolve issues.
Understand systems-related technology and theory well enough to identify issues in a timely and effective manner without jeopardizing the stability of other systems.
Provide IT support/oversight/consultation for client-facing project/contract work.
Assist our legal counsel with retaining data for targeted individuals and data sets.
Maintain and administrate Cayuse IT assets.
Maintain legacy servers for data retention.
Regular audits of all Cayuse IT assets: licenses User access roles Risk management/security User attributes
Other duties as assigned