Technical Project Manager Contract Jobs in Chicago, IL

Senior Technical Project Manager – Enterprise Integrations

Location: Chicago, IL | Hybrid – approximately 1 day onsite/week

Type: Long-Term Contract | 1+ Year

Summary

We are seeking an experienced Senior Technical Project Manager to lead a highly visible enterprise integration and digital transformation initiative for a large organization in Chicago.

This individual will step into an active, enterprise-wide program and take ownership of multiple concurrent integration projects and workstreams. The role requires someone who can quickly understand an existing environment, establish credibility with both technical and business stakeholders, and drive projects forward while managing complex dependencies, vendors, risks, timelines, and executive expectations.

This is not a deeply hands-on engineering position, but candidates should have enough technical understanding of enterprise integrations, APIs, middleware, data flows, and enterprise applications to effectively lead technical teams and communicate with architects and developers.

What You’ll Be Doing

• Lead multiple concurrent enterprise integration projects from planning through implementation and production transition
• Own project plans, schedules, milestones, dependencies, resource needs, and delivery roadmaps
• Coordinate across business stakeholders, architects, developers, application teams, vendors, consultants, and executive leadership
• Drive accountability across internal and external delivery teams
• Manage vendor deliverables, dependencies, timelines, and escalations
• Lead status meetings, planning sessions, governance reviews, and executive/steering committee presentations
• Identify and proactively manage project risks, issues, constraints, and cross-project dependencies
• Maintain RAID logs, project documentation, status reporting, action items, and decision tracking
• Coordinate testing, defect resolution, deployment readiness, cutover, go-live, and operational transition activities
• Help strengthen project governance and delivery processes across the broader program

What We’re Looking For

• 7+ years of experience leading complex technology projects or programs
• Proven experience managing large-scale, cross-functional enterprise technology initiatives
• Experience with enterprise integrations, middleware, APIs, ERP/HRIS/CRM platforms, or digital transformation programs
• Strong project planning, scheduling, dependency, risk, and issue management experience
• Demonstrated ability to manage multiple projects/workstreams simultaneously
• Experience coordinating internal technology teams, business stakeholders, vendors, and implementation partners
• Exceptional communication skills with the ability to confidently work with executive leadership as well as highly technical teams
• Strong organizational skills and the ability to bring structure, accountability, and momentum to complex programs

Highly Preferred

• Experience leading enterprise integration or middleware implementations
• Exposure to platforms such as Boomi, MuleSoft, Azure Integration Services, Informatica, TIBCO, or similar
• Experience supporting Workday, ERP, HRIS, SIS, CRM, data warehouse, financial, or other enterprise system implementations
• Familiarity with APIs, ETL, interface development, and systems interoperability
• PMP, PMI-ACP, Scrum Master, or similar certification
• Experience working within a formal PMO or governance environment

The Right Person

We’re looking for someone who can walk into a complex program already in motion, quickly understand the landscape, and confidently take ownership. You do not need to be the deepest technical expert in the room, but you should be comfortable leading conversations with architects and developers while also translating status, risks, and decisions for senior and executive stakeholders.