Hillpointe · 4 hours ago
Director of IT
Winter Park, FL
Full-time
Onsite
Director/Executive
10+ years expHillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. The Director of IT will lead the internal IT function, manage IT support, enhance cybersecurity practices, and oversee vendor relationships while ensuring scalable technology solutions across various teams.
LeasingProperty DevelopmentReal Estate
Responsibilities
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
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
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
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
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)
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
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
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
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
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
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
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
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
Qualification
Required
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
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
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
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
Company
Hillpointe
Hillpointe is a real estate development and investment management firm that controls land acquisition, land development, and construction.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Steven Campisi, CFA
Co-Founder and Managing Partner
Recent News
2025-12-15
Seattle TechFlash
2025-07-31
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