IT Director Hybrid

OverviewOur direct client, a mid-sized commercial real estate owner-operator is seeking an IT Director to lead and evolve its internal technology function. Reporting to executive leadership, this role will transition IT from a traditional support model to a more strategic, forward-thinking function, with a strong emphasis on technology optimization, scalability, and AI enablement.

This is a highly visible, hands-on leadership role offering the opportunity to own the full technology stack, shape IT strategy, influence business decisions, and modernize a complex environment - while delivering tangible AI-driven impact within the first 60-90 days.

Key ResponsibilitiesDefine and execute the organization's IT strategy and roadmap, aligning with long-term business goals and growth plansTake full ownership of the enterprise technology stack, including evaluation, consolidation, and optimization of systems to improve efficiency and scalabilityDrive AI enablement initiatives, identifying and implementing practical AI solutions (e.g., ChatGPT, Copilot) with an emphasis on near-term business value and quick winsEvaluate and recommend new tools, platforms, and enterprise solutions to enhance operational effectivenessOversee IT infrastructure, network, and security, partnering with a managed service provider (MSP) while building toward stronger in-house capabilitiesLead vendor management, including software providers and IT service partners, contract negotiation, and performance oversightProvide strategic and technical decision-making support for more complex IT initiatives and business needsOversee and mentor internal IT resources, including a Systems Administrator responsible for day-to-day support (hardware, help desk, onboarding, system access, etc.)Collaborate with executive leadership on 3-5 year strategic planning, ensuring IT is positioned to support organizational growthSupport and enhance core business systems, including custom workflows and operational platforms tied to leasing, approvals, and financial processesQualificationsProven experience leading IT functions in mid-sized or complex environments, with full ownership of systems and infrastructureStrong experience within a Microsoft ecosystem (Windows Server, O365, Azure)Hands-on experience managing and optimizing enterprise applications and tech stacks, including consolidation initiativesDemonstrated success driving IT strategy, digital transformation, and modernization effortsExperience working with and managing MSPs and third-party vendorsSolid understanding of IT infrastructure, security, and network managementExperience mentoring or managing technical staff (e.g., Systems Administrators)Strong communication skills with the ability to interface across technical and non-technical stakeholdersAbility to operate both strategically and hands-on, especially in a lean IT environmentRequired / Core Technical ExperienceExperience working in a fully Microsoft-based environmentExperience supporting and managing Microsoft Dynamics (including customized CRM workflows and business process automation)Familiarity with enterprise system integrations and data flow across platformsPreferred / Nice-to-Have ExperienceExperience with MRI Software (ERP/accounting platform commonly used in real estate environments)Exposure to tools such as Power BI, Spreadsheet Server, and other reporting/analytics integrationsFamiliarity with AI tools and licensing models (e.g., ChatGPT, Microsoft Copilot) and experience driving adoption within an organizationExperience in commercial real estate, asset-based businesses, or shopping center operationsUnderstanding of data/reporting structures (e.g., ERD concepts)

Work Environment & BenefitsHybrid Flexibility:

4 days onsite, with flexibility based on business needs

High-Impact Role:

Direct visibility with executive leadership and influence on company direction

Ownership & Autonomy:

Full responsibility for the IT function and technology decision-making

Growth Opportunity:

Opportunity to build, modernize, and scale IT capabilities in a growing organization

Collaborative Culture:

Strong cross-functional partnership across business and technology teamsApply today for immediate consideration! This is an immediate interview and hire opportunityBy applying for this job, you agree to receive calls, AI-generated calls, text messages, or emails from Benchmark IT, LLC and its affiliates, and contracted partners. Frequency varies for text messages. Message and data rates may apply. Carriers are not liable for delayed or undelivered messages. You can reply STOP to cancel and HELP for help. You can access our privacy policy here: https://bmarkits.com/privacy-policy/

Job ID:

5541