Entry Level Technical Project Manager Jobs in Chicago, IL

Job Title: Technical Project Manager (Infrastructure Migrations)

Location: Hybrid in Chicago, IL 2-3 days a week.

Pay Rate: $65.00 - $75.00 / Per Hour

Duration: 6 Months with possibility of extensions

Benefits: This position is eligible for medical, dental, vision, and 401(k).

Top 3 Must Have Skills

1.      Infrastructure & Cloud Project Management – Proven experience leading enterprise infrastructure projects, including Azure, AWS, or GCP cloud migrations.

2.      Technical Project Delivery – Strong background managing project plans, schedules, RAID logs, dependencies, and cross-functional technical teams.

3.      Executive Stakeholder Management – Experience communicating with technical teams and executive leadership, driving alignment, resolving risks, and managing competing priorities.

Top 3 Nice-to-Haves

1.      Portfolio & Resource Management – Experience balancing multiple projects, resource planning, and portfolio prioritization.

2.      Hybrid Project Delivery – Familiarity with Agile, Waterfall, and Hybrid methodologies in enterprise IT environments.

3.      PMP or Related Certification – PMP, Scrum Master, or similar project management certification preferred

Department: IT / PMO

Reports To: IT Program Manager

Overview:

We are seeking a Project Manager to join our IT team and help drive the successful execution of large-scale infrastructure and cloud migration projects. This role requires someone who understands both the technical complexity of infrastructure work (particularly in Azure/AWS/GCP environments) and the leadership skills required to support executive stakeholders in aligning resources across a dynamic portfolio of projects.

Key Responsibilities:

• Project Leadership & Execution
  • Lead infrastructure-related projects (e.g., data center migrations, cloud platform deployments, system upgrades) from initiation through closure.
  • Develop and maintain project plans, schedules, RAID logs, and communication cadences.
  • Facilitate integration across multiple workstreams (infrastructure, security, change, training) to deliver cohesive outcomes.
• Portfolio & Resource Alignment
  • Work closely with executive sponsors and department leaders to understand competing priorities and ensure efficient resource utilization across the project portfolio.
  • Help identify resource constraints early and facilitate cross-team negotiations to prevent burnout and delivery delays.
• Stakeholder Management
  • Serve as a liaison between technical teams (Infrastructure, Security) and business stakeholders.
  • Facilitate steering committee meetings, update leadership on project health, and escalate risks appropriately.
• Collaboration with Adjacent Functions
  • Partner with IT Program Manager and Change Manager to ensure technical efforts support broader business transformation goals.
  • Align with training and adoption teams to ensure smooth transition from project delivery to business-as-usual.

Preferred Experience:

• 4-6 years of experience in project management or technical leadership roles.
• Demonstrated experience leading IT infrastructure projects, preferably with cloud migration (Azure, GCP and/or AWS).
• Understanding of project delivery frameworks (Agile, Waterfall, or Hybrid), with ability to flex as needed.
• Experience managing matrixed resource teams and limited direct authority.

Ideal Candidate Traits:

• Systems-thinker who can connect technical changes to business impact.
• Comfortable facilitating across both technical and executive stakeholders.
• Proactive, organized, and thrives in ambiguity and change.
• Focused on creating repeatable processes that can scale across future projects.

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran, in accordance with applicable federal, state, and local laws. Reasonable accommodation is available for qualified individuals with disabilities upon request.