VP, Project Manager

Vice President, Project Management
Location: Chicago, IL (Hybrid)
Department: Technology Solutions
Compensation: $140,000 – $180,000 base + discretionary bonus + full benefits

The Role

We are looking for a seasoned program and project management leader to own the end-to-end delivery of enterprise technology initiatives. This is a hands-on program leadership role — not a people manager title — requiring deep expertise in full lifecycle project execution, vendor management, and executive stakeholder communication. You will serve as the primary driver of complex, multi-workstream implementations from initiation through decommissioning.

What You’ll Own

Program Leadership and Governance

• Full lifecycle ownership of technology programs from initiation through planning, execution, and closure
• Establishing and maintaining governance structures including steering committees, working groups, RACI tables, and decision logs
• Ensuring alignment with organizational goals, departmental standards, and enterprise architecture

Planning, Scheduling, and Resource Management

• Building and maintaining integrated project plans covering scope, milestones, timelines, dependencies, and critical path
• Coordinating resources across business units, technology teams, and third-party vendors
• Managing concurrent workstreams across configuration, integrations, data migration, testing, change management, training, and deployment

Vendor and Stakeholder Management

• Serving as primary liaison with external vendors, managing deliverables, SLAs, risks, and change requests
• Facilitating alignment between vendor teams and internal technical stakeholders
• Building relationships with business partners, executives, SMEs, and technology teams to ensure shared understanding at all levels

Project Lifecycle and Technical Delivery

• Partnering with functional and technical SMEs to define future-state architecture and integration requirements
• Ensuring all integration points — APIs, middleware, authentication, data flows — are documented, validated, and approved
• Overseeing system testing, integration testing, UAT, and performance testing planning and execution
• Leading cutover strategy, runbook development, and contingency planning
• Coordinating data migration activities including mapping, validation, and reconciliation
• Managing controlled decommissioning of legacy systems and post-implementation support
• Conducting lessons-learned sessions and producing project close-out documentation

Risk, Issues, and Change Control

• Identifying risks early and maintaining proactive mitigation strategies
• Facilitating issue resolution, escalation management, and decision tracking
• Maintaining change control processes for scope, schedule, and budget

Communication and Reporting

• Owning the communication plan including executive updates, team status, milestone tracking, and roadmap visuals
• Delivering concise, transparent reporting to senior leadership and cross-functional stakeholders
• Maintaining organized, accessible project documentation throughout the program lifecycle

What We’re Looking For

• 10-15 years of project and program management experience in complex technology environments
• Bachelor’s degree in Computer Science, Business, or a related field
• Expert-level proficiency in Microsoft Project — this is a hard requirement
• Strong working knowledge of Microsoft Office suite including Excel, PowerPoint, and Visio
• Demonstrated experience managing enterprise system implementations with multi-party vendor relationships
• Background in financial services or another regulated industry strongly preferred
• Exceptional written, verbal, and presentation skills — able to communicate with both technical teams and executive leadership
• Highly organized, detail-oriented, and able to manage multiple competing priorities without losing track of the critical path
• Self-directed and resourceful; comfortable operating with ambiguity and driving clarity