Director of Information Technology

The posting, as East West Hospitality wrote it

At East West Hospitality, our vision is to be the most trusted hospitality services company and employer of choice, built on genuine and enduring relationships. We believe in doing the right thing for each other, our community, our environment, and those we serve. We hope you’ll consider joining us!

Are you a forward-thinking technology leader who sees opportunities to make things better, smarter, and more efficient? East West Hospitality is seeking a Director of IT Operations to lead and evolve the technology foundation supporting our people, properties, and businesses.

East West Hospitality operates across a diverse and geographically distributed portfolio that includes hotels and resorts, homeowners associations, vacation rentals, real estate development and sales, and corporate operations. Supporting this environment requires more than reliable technology. It takes a strategic leader who understands the complexities of multiple business models and can build secure, scalable, and efficient technology operations that support both day-to-day needs and long-term growth.

Reporting to the Chief Information Officer, you'll lead the teams and strategic partners responsible for cybersecurity, infrastructure, employee technology, and company-wide IT services. This role goes beyond maintaining existing systems. You'll have the opportunity to challenge established practices, use data to identify opportunities for improvement, and rethink how technology services are delivered as business needs, automation, AI, and emerging technologies continue to evolve.

What You Will Do
Lead & Evolve IT Operations

• Develop and execute a multi-year technology operations roadmap aligned with business priorities and organizational growth.
• Identify opportunities to simplify, standardize, automate, and continuously improve technology services.
• Leverage operational data, emerging technologies, AI, and strategic partnerships to improve efficiency, service quality, and scalability.
• Partner with the CIO on technology budgets, forecasts, investments, and resource planning.
• Lead operational improvements and organizational changes with clear communication and stakeholder collaboration.

Strengthen Cybersecurity & Resilience

• Oversee operational cybersecurity, including identity and access management, threat detection, vulnerability management, and security monitoring.
• Partner with internal teams and external security experts to assess risks, establish priorities, and strengthen security practices.
• Ensure effective backup, disaster recovery, business continuity, and incident response capabilities.
• Provide leadership during significant technology or cybersecurity incidents.

Build a Reliable Technology Foundation

• Lead network, infrastructure, cloud, and shared technology services supporting offices, properties, and corporate operations.
• Oversee infrastructure improvements, technology upgrades, and lifecycle planning.
• Collaborate on technolog

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environments.

• Experience with Microsoft 365, including opportunities to improve governance, administration, adoption, and productivity.
• Demonstrated success improving technology operations, service delivery, infrastructure, or support models.
• Experience managing technology vendors, managed service providers, outsourced support teams, or strategic partners.
• Strong financial acumen, including budgeting, forecasting, vendor management, and technology investment planning.
• Ability to analyze operational data, identify trends, and turn insights into meaningful improvements.
• A genuine interest in AI, automation, and emerging technologies, with the ability to apply new capabilities thoughtfully and effectively.
• Strong communication and relationship-building skills, including the ability to engage technical teams, business leaders, and executive stakeholders.
• Proven ability to develop talent, lead change, and build high-performing teams.
• Experience supporting geographically distributed or multi-location organizations preferred.
• Hospitality, property management, real estate, or related industry experience is a plus, but not required.

Benefits & Perks
At East West Hospitality, we believe in taking care of our team members so they can thrive both personally and professionally. As a Full Time, Year Round team member, you will have access to a competitive benefits package, including:

• Medical, dental, and vision insurance
• 401(k) retirement plan
• Unlimited time off
• Annual Wellness Bonus
• Employee discounts and hospitality perks
• Opportunities for professional development and career growth
• A collaborative work environment with a diverse portfolio of businesses and talented teams

We are committed to creating an inclusive workplace where everyone feels valued, respected, and empowered to succeed. We welcome applicants from all backgrounds and experiences and make employment decisions based on qualifications, merit, and business needs.