Director, Information Technology

Ivy Hospitality is a growing hospitality management company with hotels across the Midwest, and we're looking for a Director of IT to own our technology strategy from the ground up. This is a high-impact, highly visible role. Behind every smooth check-in, every secure guest transaction, and every associate who can actually focus on hospitality instead of fighting their tech, there's an IT leader who saw the problem coming and solved it first.

That's you.

You'll set the vision, build the roadmap, and lead the systems, vendors, and security practices that keep our hotels and support office running. If you love translating business needs into smart technology decisions and can talk shop with a network engineer and a general manager in the same afternoon, we'd love to meet you.

Pay Range: $95,000 - $110,000

This is a hybrid position with 3 days in office and 2 days remote.

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Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• Develop and lead the organization's IT strategy, multi-year roadmap, and annual technology budget, aligning every investment with business goals and growth plans.
• Serve as the organization's Microsoft 365 owner and administrator, overseeing Exchange Online, Teams, SharePoint, One Drive, Entra , Intune, and related security and compliance tools.
• Lead the company-wide cybersecurity program, including policies, risk assessments, incident response, endpoint protection, access management, and security awareness training.
• Own PCI DSS compliance across all properties and the support office, partnering with operations and accounting to maintain secure payment environments.
• Direct technology vendor and managed service provider relationships, including selection, contract negotiation, performance management, integration, and billing oversight.
• Lead technology onboarding for new hotels and transitions for departing properties, ensuring systems, networks, and data are set up or transferred securely and on schedule.
• Oversee hotel technology infrastructure, including property management and point-of-sale systems, networks, guest Wi-Fi, and brand-mandated technology standards.
• Establish disaster recovery and business continuity plans and ensure they are tested and current.
• Partner with leaders across every business unit to understand their needs, translate them into practical technology solutions, and measure the results.
• Communicate technology priorities, project status, risks, and outcomes clearly to the executive team.
• Build, mentor, and lead IT staff and external resources, fostering a culture of service, accountability, and continuous improvement.

• Bachelor's degree in Information Technology, Computer Science, or a related field, or equivalent experience.
• 7+ years of progressive IT experience, including at least 3 years in an IT leadership role.
• Advanced, hands-on Microsoft 365 administration experience is required, including Entra , Intune, Exchange Online, SharePoint, Teams, and Microsoft security and compliance tools.
• Proven experience leading a cybersecurity program and maintaining PCI DSS compliance.
• Strong knowledge of networking, infrastructure, endpoint management, and cloud environments.
• Experience supporting multi-site operations; hospitality industry experience strongly preferred.
• Relevant certifications (Microsoft, CISSP, CISM, CompTIA Security+, or similar) preferred.
• Ability to interface with technical and non-technical audiences, from frontline associates to executive leadership.
• A sense of urgency, sharp attention to…