IT System Administrator - Year Round

Winter Park Resort•Winter Park, CO

5d•Onsite

About The Position

The IT Systems Administrator (ITSA) is a senior technical contributor responsible for the design, implementation, maintenance, troubleshooting, and support of Winter Park Resort’s IT infrastructure. This includes servers, cloud services, identity systems, point-of-sale platforms, mobile devices, telecommunications, storage, and related technologies. Under the direction of the Sr. Infrastructure Manager and in partnership with the IT Operations Manager, the ITSA provides advanced operational support, serves as an escalation resource for complex technical issues, and participates in local and Enterprise-level projects and initiatives. The role requires strong technical expertise, independent judgment, excellent customer service, and the ability to balance daily operations with strategic technology initiatives. The ITSA follows Winter Park Resort, Alterra, and applicable regulatory policies and procedures. The position is based primarily at Winter Park, Colorado, with occasional travel to Denver-area facilities, Alterra resorts, and other business locations. It supports a 24/7 resort operation, includes participation in on-call rotations, and requires flexibility for evenings, weekends, holidays, maintenance windows, and emergency support. The salary range is $82,000–$86,000.

Requirements

High school diploma or equivalent required.
Minimum 5 years of experience installing, maintaining, and supporting computer systems and software.
Minimum 3 years of experience in systems administration, server infrastructure, or network administration.
Demonstrated ability to independently troubleshoot complex technical issues in high-availability environments.
Valid Colorado Driver’s License required.
Strong troubleshooting, analytical, and problem-solving abilities.
Experience with Microsoft Windows, Windows Server, Active Directory, Group Policy, Entra ID, and Microsoft 365.
Working knowledge of PowerShell scripting and automation.
Experience with virtualization technologies such as VMware, Nutanix, or Hyper-V.
Experience supporting mobile devices, including iOS, Android, and Windows.
Knowledge of network technologies including TCP/IP, DNS, DHCP, VLANs, Wi-Fi, switching, and routing.
Experience with storage technologies (NAS/SAN), VoIP systems, and low-voltage cabling.
Flexibility to work evenings, weekends, holidays, maintenance windows, and provide emergency support.
Ability to lift and move up to 40 pounds with assistance.
Ability to travel throughout resort properties by walking, driving, skiing/riding, snowmobile, or ATV as needed.
Ability to work indoors and outdoors in high-altitude mountain environments.
Manual dexterity and visual and auditory acuity for operating computers, mobile devices, and technical equipment.
Ability to sit, stand, walk, bend, kneel, reach, and carry equipment for extended periods as required.

Nice To Haves

A degree in Information Systems, Computer Science, or a related field; equivalent experience is accepted.
Familiarity with Linux/Unix systems.
Familiarity with cloud platforms, SaaS applications, enterprise server systems, and infrastructure monitoring tools.
Experience with point-of-sale systems, PCI compliance, and SOX controls.

Responsibilities

Administer, maintain, monitor, and support assigned technology platforms, including servers, networking, wireless, storage, backup, telecommunications, cloud, and SaaS/IaaS solutions.
Serve as a subject matter expert for designated infrastructure systems and manage their lifecycle.
Provide advanced troubleshooting and resolution of incidents and service requests.
Participate in on-call rotations and support a 24/7 resort operation.
Maintain compliance with ITIL-based service management processes and ticketing standards.
Develop, maintain, review, and troubleshoot PowerShell scripts and automation solutions.
Participate in proof-of-concept testing, system evaluations, and technology recommendations.
Support implementation of new technologies, upgrades, and infrastructure improvements.
Work closely with IT leadership, resort departments, Enterprise IT teams, and vendors.
Maintain system documentation, inventory records, operational procedures, and technical standards.
Participate in Enterprise working groups and project teams supporting resort and corporate initiatives.
Communicate effectively with technical and non-technical stakeholders.
Follow company policies, standards, security requirements, and operational procedures.
Perform additional duties as assigned.