Director of IT Program Management & Integration

Ready to be part of something extraordinary? At Cooper's Hawk, connection is at the heart of everything we do, and we're looking for passionate people to join us. When you become part of our team, you step into a collaborative, supportive culture built on Uncompromising Hospitality, where standards and genuine care come together to create something truly unforgettable. As we continue our exciting journey, you'll help us deliver unforgettable experiences to our Wine Club Members and the entire Cooper's Hawk community.

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The Director of IT Program Management & Integration is a critical integrator role that ensures enterprise technology strategy is translated into scalable, executable, and operationally sound outcomes. This role owns the end-to-end planning, project governance, and execution framework for IT initiatives-from early demand intake and strategic planning through prioritization, delivery, operational readiness, and sustainment. The Director ensures disciplined processes, clean cross-functional handoffs, and formal validation at key milestones, enabling innovation while protecting operational stability and business value.

Partnering closely with IT leaders, Strategy & Planning, Finance, Operations, Marketing, and external vendors, this role provides structure, visibility, and accountability across the full lifecycle of technology initiatives and investments.

This position is ideal for a highly organized, business-minded IT leader who thrives at the intersection of strategy, process, and execution, and who brings clarity, rigor, and collaboration to complex, high-impact work.

How You Will Succeed:

IT Program & Portfolio Planning (End-to-End Ownership)

• Lead the definition, documentation, and continuous improvement of IT planning, intake, prioritization, and delivery processes.
• Translate enterprise and functional strategies into a clear, integrated IT roadmap with defined scope, sequencing, dependencies, and outcomes.
• Partner with Strategy and Finance to align initiatives to business priorities, funding models, and capacity constraints.
• Ensure plans are realistic, transparent, and operationally viable.

IT Project Governance & Execution Discipline

• Establish and manage IT project governance forums, stage-gates, and decision checkpoints from intake through delivery and sustainment.
• Ensure initiatives meet defined readiness criteria before progressing (e.g., funding approval, resourcing, architecture review, security, operational support).
• Provide consistent visibility into status, risks, tradeoffs, and decisions for IT and executive leadership.
• Drive accountability for scope, timelines, benefits realization, and post-launch outcomes.

Program & Project Oversight

• Oversee the IT project and program portfolio from ideation through implementation and stabilization.
• Ensure consistent application of project and program management standards (Agile, Waterfall, hybrid as appropriate).
• Identify interdependencies, risks, and capacity conflicts across initiatives; proactively drive resolution.
• Support prioritization decisions to maximize business value and minimize operational disruption.

Cross-Functional Integration & Communication

• Serve as a bridge between IT and business partners (Operations, Finance, Marketing, HR, Supply Chain).
• Translate business needs into clear, actionable technology initiatives-and translate technical implications back into business terms.
• Facilitate alignment across teams on timelines, responsibilities, and readiness expectations.
• Lead integrated planning and execution forums to ensure shared understanding and coordinated delivery.

Performance Management & Reporting

• Define and track portfolio-level KPIs and metrics (delivery health, value realization, capacity, spend, risk).
• Prepare executive- and board-level materials that clearly communicate progress, outcomes, and tradeoffs.
• Partner with Finance to ensure accurate forecasting, tracking, and reporting of IT investments.

Systems Readiness & Operational Handoffs

• Ensure solutions are operationally ready before launch, including support models, documentation, training, and sustainment plans.
• Partner with IT operations, security, and vendors to ensure smooth transitions from project delivery to steady-state support.
• Monitor post-launch performance and drive continuous improvement.

Team Leadership & Capability Building

• Lead and mentor IT program and project management resources.
• Establish clear standards, tools, and templates that improve consistency and efficiency.
• Foster a culture of collaboration, accountability, and continuous improvement.

What You Will Bring:

• Must represent Cooper's Hawk values
• 10+ years of experience in IT project, program, or portfolio management, PMO, or technology consulting.
• 5+ years leading complex, cross-functional initiatives with significant business impact.
• Proven ability to translate strategy into executable plans in high-ambiguity environments.
• Strong financial and business acumen; able to connect…