Director of IT

Hillpointe•Winter Park, FL

48d

About The Position

WHY HILLPOINTE? Hillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. Ranked at the top of NMHC's list of Builders and Developers, our team ensures best-in-class execution. Built on its long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise, enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, procurement of building materials, asset management, and capital markets. This is more than just a job - it's a career-defining opportunity! At Hillpointe, you'll be part of a dynamic, innovative team that has tangible impacts on day-to-day operations and contributes directly to overall success. Director of IT The Director of IT will lead the internal IT function and own our Microsoft tenant end-to-end, working closely with business leaders to develop, implement, and optimize secure, scalable technology across corporate, onsite property management, call center, and construction teams. The individual will be responsible for managing IT support, continuing to build out a Tier 1 helpdesk, and adapting systems and workflows to keep pace with the organization’s growth. This role will enhance cybersecurity practices, govern vendor relationships and costs, transition hardware/software inventory to ServiceNow, and align identity lifecycle to Entra ID integrated with UKG, so we can see each employee’s equipment and software during onboarding and ensure proper recovery and license removal during offboarding. We run a tight group, and this leader must be strategic and hands-on, ready to jump in with tickets, equipment provisioning (including Intune/Autopilot and Dell factory provisioning), and incident response. The Director will also guide a new Network Engineer/Cybersecurity team member on best practices.

Requirements

Bachelor’s degree in Information Technology, Computer Science, or related field; Master’s preferred.
10+ years of progressive IT experience with 5+ years in leadership, combining strategy with hands-on execution.
Demonstrated ownership of a Microsoft tenant (M365/Entra ID/Intune/Security & Compliance) and working Azure administration.
Strong, practical experience with Intune/Autopilot, Dell OEM/factory provisioning, and endpoint security baselines.
Proven success deploying ServiceNow (ITSM / ITAM / CMDB; CRM a plus) and migrating from Asset Panda or similar to ServiceNow ITAM.
Experience leading ERP programs, preferably Microsoft Dynamics-including integrations, data migration, and change management.
Depth in cybersecurity program management, EDR / SIEM operations, incident response, vulnerability management, and network security.
Experience building Tier 1 helpdesk teams, SLAs, major-incident practice, and knowledge management.
Strong vendor and contract management, budgeting, and cost optimization.
Excellent communication, documentation, and stakeholder management across corporate, properties, and construction.
Certifications (preferred): Microsoft (Entra / Intune / Azure / Power Platform), ITIL, CISSP/CCSP, Security+, MD-102/SC-900/AZ-900, and relevant ServiceNow certifications.

Nice To Haves

Knowledge of and experience with Entrata and Acumatica software is highly desirable.
Familiarity with IT service management frameworks (e.g., ITIL) and the ability to adapt them to a fast-moving, entrepreneurial environment.
SQL Server management, reporting/analytics (Power BI), and Microsoft Fabric awareness for future analytics governance.