Systems Administrator & Technology Trainer Gateway Search Associates - 5.0 Newtown Square, PA Job Details Full-time $125,000 - $150,000 a year 2 days ago Benefits Paid holidays Health insurance Dental insurance 401(k) Paid time off Vision insurance Life insurance Retirement plan Qualifications Mobile device support Teamwork Software deployment Enterprise software iOS Enterprise software support Bachelor's degree Technology management Mobile device management System deployment Property management Debugging Cross-functional communication Full Job Description 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

Pay:

$125,000.00 - $150,000.00 per year

Benefits:

401(k) Dental insurance Health insurance Life insurance Paid time off Retirement plan Vision insurance

Work Location:

Remote