Systems Administrator

The Systems Administrator plays a critical role in keeping the League’s technology running smoothly, supporting the people and systems that power PWHL’s day-to-day operations. Reporting to the Director, Information Technology and working closely with the Business Operations team, this role blends hands-on IT support with systems administration, focusing on Microsoft 365 and Okta environments, end-user device management, and cybersecurity fundamentals. It’s a great fit for someone who enjoys solving problems, supporting people, and building strong foundations as the League continues to grow. This posting is for a newly created position. The pay range for this position is $70,000 to $77,000 annually., Systems Administration & IT Support

• Provide tier 2 technical support to PWHL staff for hardware, software, network, and cloud-based service issues
• Configure, deploy, and manage end-user devices (desktops, laptops, mobile devices) using Intune
• Troubleshoot hardware and software issues, ensuring minimal downtime for staff
• Provide technical support for business applications and assist employees with IT-related issues
• Manage the relationship with the League’s helpdesk partner, ensuring timely resolution of IT support requests and escalating issues as needed
• Assist with user account management, email setup, and administrative tasks related to cloud and enterprise applications
• Other duties as assigned

Network & Cybersecurity Support

• Identify and troubleshoot network issues, escalating to and collaborating with third-party vendors as needed
• Assist in implementing security best practices, including patch management and system updates
• Support cybersecurity initiatives, such as access control, endpoint security, and phishing prevention
• Monitor and report on IT security incidents and vulnerabilities

Device Procurement & Management

• Oversee the procurement, issuance, and collection of company devices, such as laptops, tablets, and peripherals
• Maintain an inventory of IT assets, ensuring proper tracking and compliance
• Perform basic hardware setup and software installation for new employees
• Ensure all devices are properly secured, configured, and updated according to company policies

• Bachelor’s degree in Information Technology, Computer Science, Cybersecurity, or a related field
• 3+ years of experience in IT support, systems administration, or a related field
• Hands-on experience administering Microsoft 365 and Okta, or comparable enterprise identity and productivity platforms
• Experience with general IT administration, including business software, enterprise applications, and cloud-based services
• Familiarity with network troubleshooting and IT security best practices
• Experience in IT asset management and device procurement
• Strong problem-solving skills and ability to work independently
• Excellent communication and interpersonal skills to assist non-technical users
• Detail-oriented and highly organized in managing IT assets
• Flexibility to work evenings, weekends, and travel as required
• This position may be based in either the United States or Canada. Applicants must be legally authorized to work in their country of residence on a full-time basis.

Preferred Qualifications

• Experience working with third-party IT vendors for network and security support
• Familiarity with remote desktop support tools and ticketing systems
• IT certifications such as CompTIA A+, Security+, or Microsoft certifications (MS-900, MD-100)
• Experience with scripting (PowerShell, Python, Bash) for automation
• Exposure to cloud platforms such as Azure, AWS, and/or GCP
• Understanding of cybersecurity principles and best practices
• Flexibility to work evenings, weekends, and travel as required

Flexibility & Travel Candidate must be able to work remotely, with flexibility to work evenings, weekends, and travel to markets in the U.S. and Canada as required.