Director, Technical Project Management

Morgan Street Holdings • Chicago, IL

1d • $175,000 - $210,000 • Onsite

About The Position

The Director, Technical Program Management sits within tms’s Corporate Technology team and leads strategic technology initiatives across the organization. The role partners with business stakeholders, Corporate Technology leaders, project managers, and delivery teams to turn ideas into measurable outcomes, manage complex cross-functional programs from planning through implementation, and establish delivery standards, tools, and governance. Programs span ERP and finance systems, HR and workplace platforms, cloud and infrastructure modernization, data and analytics, and cybersecurity. The position requires sufficient technical understanding to challenge architecture and integration decisions, pressure-test estimates and sequencing, and hold engineering and vendor teams accountable for credible plans; it does not involve writing code.

The Director leads four Project Managers and Resource Analysts and is accountable for approximately 10–20 concurrent programs representing roughly $30 million in annual technology spend. The role combines hands-on project and program execution with leadership visibility, influencing decisions, guiding teams, improving delivery practices, and communicating portfolio health, risks, dependencies, and progress to stakeholders and Corporate Technology leadership.

In the first 90 days, the Director is expected to assess the portfolio, delivery practices, and reporting and deliver a prioritized improvement plan. By six months, a trusted portfolio-health view should be in use in executive forums. By twelve months, on-time and on-budget performance should have measurably improved, the Project Manager team should be stronger, and program standards should be consistently followed.

The role is based in tms’s Chicago office under an onsite work model. Starting salary is between $175,000 and $210,000.

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 to achieve program objectives.
• 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, including 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 activities, 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 against delivery capacity and funding.
• Develop and maintain integrated plans across multiple 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 in partnership with Finance.
• Partner with business stakeholders, architects, engineers, cybersecurity teams, infrastructure teams, and vendors to define requirements, evaluate solutions, and execute delivery strategies.
• Drive project lifecycle activities including planning, design, development, testing, deployment, cutover, and transition to support.
• Coordinate cross-functional technology teams to resolve risks, issues, dependencies, and resource constraints in a timely manner.
• Facilitate project decision-making sessions and escalate critical issues to leadership when appropriate.
• Ensure adherence to Corporate Technology standards, architecture principles, cybersecurity requirements, operational readiness processes, and governance controls.
• Manage third-party vendors and system integrators to ensure delivery commitments, timelines, quality expectations, and contractual obligations are met.
• Support vendor selection, statement-of-work development, and change-order review with Procurement and Legal, and manage vendor spend against approved budgets.
• Support change management, deployment planning, user adoption, and realization of expected business outcomes.
• Communicate project status, decisions, risks, milestones, and delivery performance clearly and transparently to stakeholders.
• Establish and maintain program management standards, templates, tools, and governance practices for consistent execution.
• Own executive governance cadence, including steering committees and portfolio review forums; frame decisions and trade-offs for senior leaders and drive follow-through.
• Standardize project planning, status reporting, RAID management, executive dashboards, and program health metrics.
• Define, track, and report delivery KPIs such as on-time and on-budget performance, forecast accuracy, scope stability, and post-implementation benefits realization, using results to drive corrective action.
• Ensure Project Managers follow established delivery processes, reporting standards, and governance requirements.
• Drive adoption and effective use of program management tools, ensuring reporting accuracy and data integrity.
• Coach and guide teams in best practices to improve delivery maturity and execution consistency.
• Continuously enhance methodologies, reporting capabilities, and automation opportunities to improve efficiency and visibility.
• 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 to support effective staffing and delivery across programs.
• Use resource data and insights to support program planning, 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 company match and profit sharing.
• 15 days of paid time off plus company holidays.
• Tuition reimbursement and student loan repayment assistance.
• Inclusive employee resource groups.
• Compensation, recognition, learning and development, corporate citizenship, and work-life balance programs.

What This Job Offers

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