IT System Administrator - Year Round (On-Site)

About the role

Year Round

Perks & Benefits

• Free season pass to Winter Park and all Alterra Resorts
• Discounted friends & family tickets
• Medical, dental, vision, life, paid parental leave and more for eligible employees
• 401(k) plan with 100% company match - up to 4%
• Mental health resources for all employees
• Food & beverage and retail discounts
• Onsite employee childcare based on availability
• Discounted equipment rentals, pro-deals, and more

ATTN: To be considered, resume and cover letter are required.

Position Summary

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, including servers, cloud services, identity systems, point-of-sale platforms, mobile devices, telecommunications, storage, and related technologies.

Working 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 day-to-day operations with strategic technology initiatives.

The ITSA follows all Winter Park Resort, Alterra, and applicable regulatory policies and procedures.

Wage

The base salary pay range below represents the low and high end of Winter Park Resorts' salary pay range for this position. Actual pay will vary and may be above or below the range based on various factors including but not limited to experience, education, training, location, merit system, quantity or quality of production, responsibilities, and regular and/or necessary travel. The range listed is just one component of Winter Park Resorts' total compensation package for employees. Other rewards may include many region-specific benefits.

Salary pay range: $82,000 - $86,000

Essential Duties

Infrastructure Administration & Support

• 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.

Automation & Technical Development

• 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.

Collaboration & Documentation

• Work closely with IT leadership, resort departments, Enterprise IT teams, and vendors.
• Maintain thorough 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.

Operational Expectations

• Work a standard schedule while maintaining flexibility for evenings, weekends, holidays, maintenance windows, and emergency support.
• Follow all company policies, standards, security requirements, and operational procedures.
• Perform additional duties as assigned.

Education & Experience

Education

• High School Diploma or equivalent required.
• Degree in Information Systems, Computer Science, or related field preferred; equivalent experience accepted.

Experience

• 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.

Qualifications & Technical Skills

• 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.
• Familiarity with Linux/Unix systems preferred.
• Experience supporting mobile devices (iOS, Android, 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.
• Familiarity with cloud platforms, SaaS applications, enterprise server systems, and infrastructure monitoring tools.
• Experience with point-of-sale systems, PCI compliance, and SOX controls preferred.

Travel Requirements

Primary work location is Winter Park, Colorado. Occasional travel to Denver-area facilities, Alterra resorts, and other business locations may be required.

Work Environment & Physical Requirements

• Ability to lift and move up to 40 pounds with assistance.
• Ability to travel throughout resort properties via walking, driving, skiing/riding, snowmobile, or ATV as needed.
• Ability to work indoors and outdoors in high-altitude mountain environments.
• Manual dexterity and visual/auditory acuity required for operation of computers, mobile devices, and technical equipment.
• Ability to sit, stand, walk, bend, kneel, reach, and carry equipment for extended periods as required.