Director, Technical Project Management

Morgan Street • Chicago, IL

3d • Onsite

About The Position

The Director, Technical Program Management sits within the Corporate Technology team and leads strategic technology initiatives in partnership with business stakeholders, Corporate Technology leaders, project managers, and delivery teams. The role turns ideas into measurable outcomes by driving complex, cross-functional programs from planning through implementation and establishing standards, tools, and governance for consistent delivery. Program areas include ERP and finance systems, HR and workplace platforms, cloud and infrastructure modernization, data and analytics, and cybersecurity.

The position leads four Project Managers and Resource Analysts and is accountable for a portfolio of approximately 10–20 concurrent programs representing roughly $30 million in annual technology spend. It combines hands-on project and program execution with leadership visibility, including oversight of project health, risks, dependencies, budgets, and progress. The role requires technical depth to assess architecture and integration decisions, estimates, sequencing, and delivery plans, without writing code.

In the first year, the Director is expected to assess the portfolio and delivery practices and prioritize improvements; establish a trusted portfolio-health view used in executive forums; and measurably improve on-time and on-budget delivery, team capability, and consistent use of program standards. The position is based onsite at the company’s Chicago office.

Requirements

• Bachelor’s degree in Information Technology, Computer Science, Engineering, Business, or a related field.
• 15+ years of experience leading complex technology projects and programs, including 5+ years directly managing project or program management staff.
• Proven experience delivering large-scale, cross-functional technology initiatives involving multiple stakeholders, teams, and vendors.
• Strong knowledge of Agile, Waterfall, and Hybrid project and program management methodologies.
• Experience developing integrated program plans and managing scope, schedule, budget, risks, issues, dependencies, and change requests.
• Experience coordinating application, infrastructure, cybersecurity, data, and vendor workstreams.
• Strong stakeholder management skills and ability to influence business leaders, Corporate Technology leaders, and delivery teams.
• Experience creating executive-level reporting, dashboards, program health metrics, and status communications.
• Experience owning multi-million-dollar technology program budgets, including forecasting, variance analysis, and partnering with Finance.
• Experience defining and reporting delivery KPIs, such as on-time and on-budget performance, forecast accuracy, and benefits realization.
• Experience establishing and enforcing program management standards, governance practices, templates, tools, and reporting frameworks.
• Experience leading resource planning, including capacity management, utilization analysis, and time-tracking processes.
• Demonstrated ability to lead, coach, and mentor Project Managers, Resource Analysts, and program support resources.
• Strong analytical, problem-solving, communication, and organizational skills.
• Experience managing vendor relationships and holding implementation partners accountable for delivery commitments.

Nice To Haves

• PMP, PgMP, Agile, Scrum, or related project management certification.
• Experience with ServiceNow, Jira, Azure DevOps, Microsoft Project, or similar delivery and reporting tools.
• Experience leading enterprise technology transformation, infrastructure, digital, cybersecurity, ERP, or SaaS initiatives.
• Experience leading enterprise-wide PMO build-out or delivery-transformation efforts.

Responsibilities

• Coordinate end-to-end delivery of complex Corporate Technology programs and projects from initiation through implementation, stabilization, and benefits realization.
• Partner with Corporate Technology leadership on demand intake, portfolio prioritization, and roadmap sequencing, balancing business priorities with delivery capacity and funding.
• Develop and maintain integrated plans across workstreams, aligning scope, schedule, budget, resources, dependencies, and business objectives.
• Own program and project budgets, including estimates, forecast-versus-actual tracking, capital and operating costs, variance reporting, and funding decisions with Finance.
• Partner with business stakeholders, architects, engineers, cybersecurity and infrastructure teams, and vendors to define requirements, evaluate solutions, and execute delivery strategies.
• Drive projects through planning, design, development, testing, deployment, cutover, and transition to support.
• Coordinate cross-functional teams and resolve risks, issues, dependencies, and resource constraints; facilitate decisions and escalate critical issues to leadership.
• Ensure adherence to Corporate Technology standards, architecture principles, cybersecurity requirements, operational readiness processes, and governance controls.
• Manage third-party vendors and system integrators to meet delivery commitments, timelines, quality expectations, contractual obligations, and approved budgets.
• Support vendor selection, statements of work, and change-order reviews with Procurement and Legal.
• Support change management, deployment planning, user adoption, and realization of expected business outcomes.
• Communicate project status, decisions, risks, milestones, and delivery performance to stakeholders.
• Establish and maintain program management standards, templates, tools, and governance practices across initiatives.
• Own executive governance cadence by running steering committees and portfolio reviews, framing decisions and trade-offs for senior leaders, and following through on decisions.
• Standardize project planning, status reporting, RAID management, executive dashboards, and program health metrics.
• Define, track, and report delivery KPIs, including on-time and on-budget performance, forecast accuracy, scope stability, and benefits realization, and use results to drive corrective action.
• Ensure Project Managers follow delivery processes, reporting standards, and governance requirements; drive effective use of program management tools and reporting data integrity.
• Coach teams and improve delivery maturity, methodologies, reporting capabilities, and automation opportunities.
• Manage, mentor, and develop a team of four Project Managers and Resource Analysts, fostering accountability, collaboration, continuous improvement, and delivery excellence.
• Oversee time-reporting processes and use resource data to support staffing, capacity, prioritization, and delivery decisions.
• Promote consistent resource management practices, reporting standards, and operational discipline across Corporate Technology.

Benefits

• Generous medical, dental, vision, and other benefits.
• Paid parental and medical leave programs.
• 401(k) with a company match component and profit sharing.
• 15 days of paid time off plus company holidays.
• Tuition reimbursement and student loan repayment assistance.
• Inclusive employee resource groups.

What This Job Offers

• Job Type: Full-time
• Career Level: Director