Are you a tech-savvy systems professional looking for an unconventional role that takes you out of the standard corporate cubicle?
• Remote-first, with a strong preference for candidates living within 1–2 hours of the Philadelphia suburbs for monthly in-office collaboration (1–2 times per month).
• Approximately 25% travel - U.S. and potentially Europe.
We are seeking a Systems Administrator & Technology Trainer to oversee, optimize, and scale the operational platforms powering an exclusive, high-end property portfolio. Reporting directly to a Principal, this unique role sits at the intersection of enterprise systems administration, elite hospitality tech, and hands-on workforce enablement.
If you love mastering specialized software, managing Apple-centric ecosystems, and traveling to luxury destinations to train teams, this is your next adventure.
System Administration & Architecture
• Serve as the sole administrator for specialized property and operations management software.
• Manage user permissions, onboard new profiles, and maintain a clean, scalable data architecture.
• Ensure flawless integration of operational platforms across field-deployed iPhones, iPads, and corporate iCloud environments.
On-Site Enablement & Training
• Conduct dynamic, hands-on training sessions (both remote and on-site during travel) to help non-technical staff master workflows.
• Bridge the gap between corporate technology goals and real-world property operations.
• Proactively audit platform workflows to eliminate friction and maximize communication efficiency between global teams.
Requirements
• Bacelor's degree with 5+ years experience
• Strong background administering business software, with a major plus for experience in CMMS, property management, facilities management, or estate systems.
• Deep familiarity with managing iOS, iPadOS, and iCloud deployment in a business or team environment.
• Exceptional communication skills and the patience to translate complex technical concepts into simple instructions for non-technical users.
• A natural curiosity to troubleshoot bugs, resolve edge-case user errors, and constantly improve workflows.
Benefits Competitive salary and benefits package: 100% employer-paid benefits for the employee and family. 9% 401(k) contribution. 3 weeks PTO, generous paid holiday schedule