VP, Head of Project Management

Location: Chicago, IL (4 days a week in office)

Role Overview: The organization is evolving its project management function toward an enterprise-wide leadership structure designed to enhance operational coherence, portfolio transparency, and more effective capital allocation and execution at scale. The Head of Project Management will lead this transformation by consolidating up to 20 project management professionals into a federated center of excellence while owning enterprise portfolio governance and Executive Leadership Team (ELT) reporting. The role operates across a complex, regulated, multi-entity environment and requires a leader who is equally comfortable shaping strategy at the executive level and driving successful delivery across the organization. In This Role You'll Be Responsible For: Leadership & Organizational DesignDesign and evolve an enterprise-wide PM operating model, aligning practitioners currently embedded across business and support functions into a more coordinated structure through influence and stakeholder engagement. Define the target operating model for the consolidated PM function, including governance structures, career frameworks, and integration with existing business unit delivery structures. Sequence the transition of PM responsibilities from distributed teams, ensuring continuity of execution and appropriate capacity at each stage. Lead, mentor, and develop project managers; establish formal succession plans, structured Learning & Development (L&D) pathways, and clear performance expectations and accountability models. Foster a culture of collaboration, ownership, and continuous improvement.

Program Execution & Strategy: Lead end-to-end program delivery, embedding strong change management and execution discipline across the portfolio. Partner with business leaders to align and prioritize roadmaps, driving strategy execution through consistent frameworks, governance, and KPI-based tracking. Promote transparency through metrics-led reporting, enabling faster and more informed decision-making. Align programs to growth, innovation, and risk objectives while harmonizing execution across functions.

Project Management Methodology & Tooling: Design and govern a federated PM model that balances enterprise-wide standards and portfolio visibility with domain-aligned delivery effectiveness. Establish enterprise portfolio visibility mechanisms, enabling transparent prioritization and resource allocation at the Executive Leadership Team (ELT) level. Define how projects are tracked and communicated consistently across regions and disciplines (software, infrastructure, operations, etc.).Enforce execution discipline through right-sized meetings, timely decision-making, effective escalation paths, and efficient communication to boards, executives, and stakeholders. Drive continuous improvement of PM practices by leveraging AI, Jira, Confluence, and a culture of learning and continuous improvement.

Financial & Resource Management: Develop, manage, and monitor program budgets in partnership with support functions. Build a framework to forecast, track, and allocate resources and effort across the enterprise, optimizing delivery and value realization. Model capacity requirements tied to consolidation timing, ensuring the function remains appropriately resourced throughout the transition. Define, track, and report on KPIs, benefits realization, and delivery health at the executive level.

Stakeholder & Executive Engagement: Serve as the primary point of contact for senior leaders, executive sponsors, and cross-functional partners. Facilitate alignment across business, technology, operations, risk, and regulatory stakeholders, bridging gaps between technical and business teams. Navigate entity-specific constraints across multiple international legal entities, balancing enterprise PM standards with local regulatory requirements.

Risk Management & Controls: Identify, assess, and manage program risks, dependencies, and issues; implement mitigation strategies and escalation paths consistent with the organization's risk and compliance standards. Ensure programs adhere to regulatory, operational, and internal control requirements.

Experience: Proven track record leading large-scale programs or portfolios in a complex, regulated environment (financial services, exchanges, fintech, or capital markets). Prior experience leading a PM consolidation or organizational transformation is strongly preferred. Leadership: Demonstrated ability to grow teams, influence across organizational boundaries, and manage change in a matrixed environment. Strategic Thinking: Ability to translate enterprise strategy into executable programs with measurable outcomes, operating at both transformation and steady-state levels simultaneously. Communication: Exceptional written and verbal communication skills, including executive-level reporting and stakeholder engagement. PM Expertise: Proficiency with enterprise PM tools (e.g., Jira Programs, Jira Plans), AI-augmented delivery, and project management methodologies.