Director of IT Program Management and Integration

Are you ready to be part of something extraordinary? At Cooper's Hawk, connection is at the heart of everything we do, and we're on the lookout for passionate individuals to join our team. By becoming a part of our collaborative and supportive culture, built on Uncompromising Hospitality, you'll play a vital role in delivering unforgettable experiences to our Wine Club Members and the entire Cooper's Hawk community. Join us in transforming moments into lasting memories. The Director of IT Program Management and Integration is a pivotal role that bridges enterprise technology strategy with actionable outcomes. This leader will oversee the entire planning process, project governance, and execution for all IT initiatives—from initial demand intake to strategic planning, prioritization, delivery, operational readiness, and sustainment. This position ensures processes are disciplined with clear cross-functional collaboration and validation throughout key milestones, fostering innovation while maintaining operational stability and business value. Working hand-in-hand with IT leaders, Strategy & Planning, Finance, Operations, Marketing, and external vendors, this role will establish structure and visibility guided by accountability across the lifecycle of technology initiatives and investments. This position is perfect for a highly organized, business-savvy IT leader who excels at navigating the intersection of strategy, process, and execution, bringing clarity, rigor, and collaboration to complex, high-impact projects. Key Responsibilities: IT Program & Portfolio Planning: Lead the creation, documentation, and continuous enhancement of IT planning, intake, prioritization, and delivery processes. Transform enterprise and functional strategies into a cohesive IT roadmap that clearly defines scope, sequencing, dependencies, and expected outcomes. Align initiatives with business priorities, funding models, and capacity constraints in collaboration with Strategy and Finance. Ensure all plans are realistic, transparent, and operationally viable. IT Project Governance & Execution: Establish and manage IT project governance frameworks, stage-gates, and decision checkpoints from initiation through delivery. Ensure all initiatives meet defined readiness criteria before advancement. Provide consistent updates into status, risks, tradeoffs, and decisions for IT and executive leadership. Maintain accountability for scope, timelines, benefit realization, and post-launch evaluations. Program & Project Oversight: Oversee the entire IT project and program portfolio from ideation to implementation and stabilization. Ensure consistent application of project and program management methodologies (Agile, Waterfall, hybrid as necessary). Identify interdependencies, risks, and capacity conflicts across initiatives and drive proactive resolution. Support prioritization to maximize business value while minimizing operational disruptions. Cross-Functional Integration & Communication: Act as a connector between IT and various business units (Operations, Finance, Marketing, HR, Supply Chain). Translate business needs into actionable technology initiatives and clarify technical implications in business terms. Facilitate team alignment on timelines, responsibilities, and readiness expectations. Lead integrated planning and execution meetings to ensure a shared understanding and coordinated efforts. Performance Management & Reporting: Establish and monitor portfolio-level KPIs and metrics (delivery health, value realization, capacity, expenditure, risk). Prepare comprehensive executive and board-level materials that outline progress, outcomes, and tradeoffs. Collaborate with Finance to maintain accurate forecasting and reporting of IT investments. Systems Readiness & Operational Handoffs: Ensure solutions are operationally ready at launch, including support models, documentation, training, and sustainment plans. Collaborate with IT operations, security, and vendors for smooth transitions from project delivery to steady-state support. Monitor post-launch performance and promote continuous improvement. Team Leadership & Capability Building: Lead and mentor IT program and project management teams. Develop standards, tools, and templates for enhanced consistency and efficiency. Encourage a culture of collaboration, accountability, and ongoing improvement. What You'll Bring: Alignment with 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. Demonstrated ability to convert strategy into actionable plans in high-ambiguity settings. Strong financial and business acumen; adept at linking technology investments to enterprise value. In-depth knowledge of project and program management methodologies (Agile, Waterfall, hybrid). Outstanding communication skills, capable of effective storytelling and decision-making narratives at the executive level. Experience in multi-unit restaurant, retail, or hospitality environments is highly preferred. Bachelor's degree in Information Technology, Business Administration, or a comparable field (or equivalent experience). Other Abilities: Program & Process Design: Develop scalable planning and project governance frameworks. Operational Rigor: Ensure solutions are practical and supportable in production environments. Portfolio Thinking: Manage demand, capacity, risk, and value across competing needs. Cross-Functional Influence: Align IT, business, and vendor partners even without direct authority. Decision Quality: Foster clarity, tradeoffs, and timely decisions in complex scenarios. Communication: Deliver clear, concise reports and updates for executives and stakeholders. Compensation Range: $150,000-$175,000 + bonus potential. The final offered salary will reflect multiple factors including the candidate's experience, skills, qualifications, and internal pay equity. What You'll Get: Incredible Discounts: Monthly Dining Allowance 50% Dining and Carryout 40% Retail Wine 20% Retail and Private Events Monthly Complimentary Wine Tasting for Two Medical, Prescription, Dental, Vision Insurance plus Telemedicine and Wellness Program Company Matching 401(k) Retirement Savings Plan Flexible Savings Accounts- Health and Dependent Care Health Savings Account Long-Term Disability; Voluntary Short-Term Disability Basic Life and AD&D Insurance (with option to purchase additional coverage) Paid Parental Leave Highly Competitive Pay plus Team Member Incentives & Rewards Paid Time Off Milestones Recognition Program Complimentary Gym Membership in RSC Building Hybrid Work Week (3 days in office, 2 days remote, depending on role) Cooper's Hawk is an equal opportunity employer. All qualified applicants are considered for employment without regard to the person's race, color, religion, national origin, sex, sexual orientation, age, marital status, veteran status, disability, or any other characteristic protected by applicable law. Cooper's Hawk makes reasonable accommodations during all aspects of the employment process, including during the interview process. The information provided above indicates the general nature and level of work required for the position and is not a comprehensive list of all responsibilities or qualifications. The Benefits list is a highlight of some of the benefits offered to team members; eligibility for certain benefits may vary. About Us Cooper's Hawk features a Napa-style tasting room with wine-inspired retail for entertaining and a full-service restaurant, bar, and private event space, offering a modern yet casual dining experience. Each scratch-kitchen menu item is designed to pair perfectly with our wines. Speaking of wine...the Cooper's Hawk Wine Club is perhaps the largest in the world, offering not just award-winning wines but also exclusive membership benefits, including curated dining and travel experiences. Since our inception in 2005, we have brought the Napa Valley experience to our guests and Wine Club members, and with the launch of Piccolo Buco by Cooper's Hawk, we are now sharing the vibrant flavors of Rome with them as well. Together, we are creating a lifestyle brand like no other.

Created: 2026-03-10