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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of IT Program Management & Integration - **Company:** Cooper's Hawk Winery & Restaurants - **Location:** Downers Grove, IL, United States - **Experience:** Expert - **Salary:** $150,000.0 - $175,000.0 - **Contract:** Permanent contract - **Skills:** Agile Methodology, Information Technology Consulting, IT Management, Information Technology Operations, Systems Integration, Information Technology - **Published:** May 15, 2026 - **Apply:** https://www.indeed.com/viewjob?jk=1143434fc24e6018 ## About the Role Do you have experience in Managerial strategic planning?, Do you have a Bachelor's degree?, * 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 technology investments to enterprise value. * Deep understanding of project and program management methodologies (Agile, Waterfall, hybrid). * Exceptional communication skills, including executive-level storytelling and decision framing. * Experience in multi-unit restaurant, retail, or hospitality environments strongly preferred. * Bachelor's degree in Information Technology, Business Administration, or related field (or equivalent experience). ## Description 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. ## Related Videos - [Your Manager Doesn’t Come with a User Manual (But You Can Totally Write One)](https://www.wearedevelopers.com/videos/1495-your-manager-doesn-t-come-with-a-user-manual-but-you-can-totally-write-one) - [Crew Management System for Airlines: Plan duties for pilots & flight attendants worldwide](https://www.wearedevelopers.com/videos/1444-crew-management-system-for-airlines-plan-duties-for-pilots-flight-attendants-worldwide) - [ShapeShift: Reinventing Agile for a B2B SaaS Scale-Up](https://www.wearedevelopers.com/videos/1655-shapeshift-reinventing-agile-for-a-b2b-saas-scale-up) - [AI Agents & Agentic AI](https://www.wearedevelopers.com/videos/2017-ai-agents-agentic-ai) - [Unveiling the Dark Side: Navigating the Pitfalls of Digital Ambitions](https://www.wearedevelopers.com/videos/666-unveiling-the-dark-side-navigating-the-pitfalls-of-digital-ambitions) - [Engineering/Manager Pendulum: Generating compound interest on your career](https://www.wearedevelopers.com/videos/100348-engineering-manager-pendulum-generating-compound-interest-on-your-career) ## Related Articles - [7 Important Tips That Every Software Developer Should Know](https://www.wearedevelopers.com/magazine/101-7-important-tips-that-every-software-developer-should-know) - [From developer to manager – what does it take to become an engineering manager?](https://www.wearedevelopers.com/magazine/42-from-developer-to-manager-what-does-it-take-to-become-an-engineering-manager) - [Should Tech Managers Be Developers First? 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