Director of IT

Company: Hillpointe
Location: Winter Park
Posted on: February 16, 2026

Job Description:

Job Description Job Description 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. Key Responsibilities IT Infrastructure Management: Analyze and optimize IT infrastructure and systems performance to align with the fast-paced needs of the business. Develop scalable endpoint and network standards and Intune/Autopilot provisioning patterns (with Dell OEM/factory support) that enable direct-to-user deployment and consistent security baselines. Coordinate regular maintenance, patching, and lifecycle refresh to ensure availability and minimal downtime across corporate and property sites. Cybersecurity Strategy and Risk Management: Develop and implement a comprehensive cybersecurity strategy to protect data, identities, endpoints, email, and networks. Identify and remediate risks and vulnerabilities, implement secure configurations, and lead ongoing awareness training. Operate and tune Microsoft Defender XDR and Microsoft Sentinel, define incident response playbooks, and oversee investigations and post-incident reviews. Mentor the Network Engineer/Cybersecurity hire on firewall hygiene, EDR/alert tuning, detections, forensics, and response best practices. Business Continuity Planning: Design and implement BCP/DR protocols - RPO/RTO definitions, backup and recovery testing, failover runbooks, and crisis communication - scaled for highly dynamic operations across corporate, onsite property management, call center, and construction teams. Helpdesk and Team Development: Lead the creation and management of a Tier 1 helpdesk to support ERP / line-of-business applications and core productivity tools. Establish SLAs, escalation paths, a major incident framework, and knowledge management. Coach technicians on customer experience, documentation, and automation; personally assist with escalations when needed. Vendor and Contract Management: Own all third-party vendor relationships - negotiate terms, track costs, renewal dates, and named users, and drive continuous improvement in service quality and price. Maintain a central vendor catalog and entitlement register (licenses, contracts, device warranties, carrier circuits). Hold direct relationships with Microsoft (M365, Azure, Fabric) and Dell (procurement and provisioning). Budgeting and Resource Allocation: Develop and manage the IT budget, including cloud subscriptions, Microsoft licensing, hardware refresh, carrier services, and tools (ServiceNow, security). Track spend and identify opportunities for license rightsizing and reclamation and smarter procurement to reduce total cost of ownership without sacrificing reliability. Strategic Planning and IT Capacity Management: Collaborate with leadership to align IT strategy to growth and operational priorities. Use capacity planning, telemetry, and KPIs to ensure infrastructure, endpoints, service desk, and security functions scale effectively. Translate strategy into clear quarterly plans, deliverables, and executive reporting. IT & Cybersecurity Auditing: Perform regular IT and security audits against policy and industry frameworks; maintain remediation backlogs with due dates and evidence. Ensure audit readiness for software licensing, device custody, access control, backups, and incident response. Microsoft 365 Administration and Support: Administer and support the Microsoft 365 suite (Exchange, Teams, SharePoint, OneDrive, Power BI, Planner) and govern Power Platform (Power Apps/Automate) including environments, DLP, connectors, and lifecycle. Provide user access management, license optimization, and adoption guidance to maximize business value. Microsoft Tenant Ownership & Identity Lifecycle: Serve as primary owner of the Microsoft tenant, responsible for Entra ID (identity governance, SSO, Conditional Access, MFA, PIM), Intune (Windows / iOS / iPadOS / Android), Security & Compliance (DLP/Retention/Records/eDiscovery), and Secure Score improvements. Implement joiner-mover-leaver automation with Entra ID Lifecycle Workflows integrated with UKG to: Create/disable accounts, assign/revoke licenses, and manage group / Teams access. Present a single view of assigned equipment and software access for onboarding and offboarding, with auditable license reclamation and hardware recovery. ServiceNow Platform: CRM ? ITSM & ITAM Transition: Assist on the 2026 rollout of ServiceNow CRM, followed by Helpdesk / ITSM (incidents / requests / problem / change) and IT Asset Management (HAM / SAM) replacing our current inventory and asset tracking platform, Asset Panda. Stand up CMDB relationships, lifecycle states, tagging/barcoding, stockrooms/RMA, and software entitlement tracking with usage insights for cost recovery. Integrate monitoring, Intune/device data, and identity data for end-to-end visibility. Hardware Provisioning & Field Deployment: Establish standard images / profiles and Autopilot configurations; leverage Dell factory provisioning for direct-ship devices with minimal IT touch. Maintain efficient depot, spares, and warranty / RMA management to support field and corporate operations. IT Asset Management (Hardware & Software): Implement and govern ServiceNow ITAM for hardware (HAM) and software (SAM), with a clean CMDB, lifecycle workflows, and periodic inventories. Track entitlements vs. usage, reclaim idle licenses, and maintain audit-ready evidence across all software and devices. Real Estate and Multifamily Experience (Preferred): Experience supporting property management, leasing, maintenance, access control, and property network/connectivity needs. Familiarity with Entrata and Acumatica is advantageous; ability to integrate/re-platform to Dynamics and related apps is highly desirable. Qualifications 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. Preferred Experience: 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. Physical Requirements Incumbents must be able to physically access all exterior and interior parts of the community and amenities. Incumbents must be able to push, pull, lift, carry, or maneuver weights of up to twenty (20) pounds independently and fifty (50) pounds with assistance. Routine local travel may be required to make business meetings, attend training classes, conferences, or other situations necessary for the accomplishment of some or all of the daily responsibilities of this position. Work Environment: This role primarily operates in an office environment with occasional travel to project sites or external meetings. Some exposure to outdoor elements may occur during site visits. Primarily in an office setting with prolonged periods of sitting at a desk and working on a computer. Ability to move within an office environment, including accessing file cabinets, meeting rooms, and office equipment. Required Licenses or Certifications: Incumbents must have all licenses and/or certifications as required by State and Local jurisdictions. Incumbents must have valid driver's license to drive while visiting property. NOTE: This document outlines the general nature and level of work expected from individuals in this role. It's important to understand that this is not an exhaustive list of responsibilities, duties, and skills. Additional tasks or job functions that can be safely performed may be required as necessary by supervisory personnel. This flexibility in additional duties showcases the company's adaptability and encourages employees to be versatile. The employee is expected to adhere to all work rules, procedures, and policies established by the company, including, but not limited to, those contained in the employee handbook.

Keywords: Hillpointe, Daytona Beach , Director of IT, IT / Software / Systems , Winter Park, Florida