Description:

Join our team! Windsor Hospitality thrives in building hospitality careers We are seeking a driven and technically sharp IT Systems & Technology Specialist to help co-own our technology infrastructure and lead the modernization of how our organization uses software and artificial intelligence. This is a hands-on individual contributor role for someone who thrives at the intersection of practical IT operations and forward-thinking innovation. You will assist and be a resource across the organization — keeping systems running, driving AI adoption, and building a more efficient, modern technology foundation.

Where this role is located:

This position is based out of our HQ office located in Santa Monica, CA. There is some travel required to our portfolio of hotels on a as needed basis. 

Essential Responsibilities

Hotel Brand Technology Compliance

· Co-lead support to ensure all properties remain compliant with Hilton/Marriott brand technology standards and requirements.

· Assist as needed the on-property point of contact for Marriott-mandated system audits and technology assessments.

· Assist in communicating brand-technology updates and requirement changes to property leadership and the corporate IT team.

· Assist to maintain documentation of brand compliance status across the portfolio.

On-Call & Field Support

· Co-lead IT resource for property-level technology emergencies across the portfolio.

· Assist in providing first-line technical support to General Managers and property staff for day-to-day IT issues.

· Respond to property support requests in a timely manner with clear communication on status and resolution timelines.

· Assist to Log and document all field support interactions and resolutions in the ticketing system for corporate IT visibility.

· Assist in correcting complex or infrastructure-level issues with clear documentation and context.

IT Systems and Infrastructure 

• Assist to serve as a technical resource providing Tier 2/3 support and infrastructure management across all locations.

• Provide support for Windows operating systems, Microsoft 365, hardware, software, printers, and peripheral equipment.

• Help manage cloud infrastructure (Microsoft 365 environment) including security, cost optimization, and user access.

• Set up and maintain user accounts, email, permissions, and licensing within the Microsoft 365 environment.

• Assist with Installation, configuration, and maintenance for desktop, laptop, and peripheral equipment.

• Help develop policies and procedures required to ensure IT compliance. 

Asset Management & Inventory Controls

· Co-lead owning and maintaining a centralized IT asset tracking system for all hardware and software assets across corporate and field locations.

· Assist to implement and enforce asset lifecycle management processes — from procurement and deployment through maintenance, refresh, and decommission.

· Conduct regular physical and digital audits of IT assets across the organization to ensure accuracy of inventory records.

· Assist to track software licensing, renewals, and compliance to prevent gaps or over-spend across all platforms and subscriptions.

· Co-lead to establish standardized procedures for asset tagging, check-in/check-out, and chain of custody for all IT equipment.

· Partner with finance and operations to support budgeting for hardware refresh cycles and technology procurement per brand standards. 

· Coordinate with the Field maintain accurate property-level asset records across all 9 hotel properties.

· Co-lead to generate regular asset and inventory reports for leadership visibility into technology spend, utilization, and lifecycle status.

· Help lead disaster recovery planning, business continuity strategy, and incident response.

· Assist in managing vendor relationships, licensing agreements, and technology procurement.

Software & Systems Modernization

• Co-lead Define and execute a technology roadmap aligned with business goals, with emphasis on software modernization and AI integration.

• Evaluate and guide architecture decisions for internal platforms and third-party integrations.

• Establish and enforce systems utilization standards, security policies, and best practices.

• Maintain ticketing system workflows and contribute to the knowledge base and documentation standards.

Skills and abilities you bring: 

The individual must possess the following knowledge, skills and abilities to efficiently and properly execute the essential functions of the job

• Strategic      thinking implemented through short-term execution.
• Extremely organized, detail oriented, with the ability to multitask with minimal supervision.
• Ability to communicate effectively, eloquently, verbally and in writing.
• Ability to communicate and direct technically with onsite vendors is a must.
• Must demonstrate patience and professionalism at all times. 
• Proven ability to troubleshoot complex hardware/software issues. 
• Ability to effectively communicate with and collect information from team members and third parties, some of whom      will require high levels of tact and/or diplomacy. 
• No job too small or too big mentality (any unassigned miscellaneous tasks for office you “own”).
• Reachable and willingness to engage after hours or weekends with a fast response time.

Technical Knowledge:

• Expertise in Microsoft Windows, Office 365, server administration, network protocols      (LAN/WAN)'
• Experience with LLM-based tooling, AI APIs, or building AI-assisted workflows.
• Experience with ServiceDesk Plus Ticketing and asset management system.
• CompTIA A+, Microsoft certifications, or similar credentials.
• CompTIA Network + and CompTIA Security +
• Experience supporting multi-site and distributed work environments.
• Experience with Cisco Meraki and Netgear switches and routers.
• Experience with MDF configurations
• Knowledge of Copper and fiber-based infrastructure.

What we offer:

Join a team that invests in you! We’re proud to offer a comprehensive and competitive benefits package to support the well-being and growth of our eligible employees in our diverse and inclusive environment:

• Medical, Dental, Vision, Life and Disability Insurance if eligible, enjoy access to quality healthcare plans to stay healthy and protected.
• Flexible Spending Account (FSA) Pre-tax savings for healthcare and dependent care expenses.
• 401(k) & Roth 401(k) Plans Plan for your future with employee-supported retirement options.
• Employee Assistance Program (EAP) Confidential support services for personal and professional well-being.
• Career Growth Opportunities We promote from within and invest in your long-term success.
• Paid Time Off (PTO) Take time to relax, recharge, and explore life outside of work.
• Paid Sick Leave Supportive sick time policy to care for your health when you need it.
• Exclusive Employee Hotel Discounts Take advantage of special rates for hotels in our brand portfolio – just for our team members and their family and friends.
• Recognition & Rewards Program Our team members are regularly acknowledged through performance awards, milestone celebrations, and incentive programs that recognize excellence and dedication.