Senior Technical Project Manager – Infrastructure & Enterprise Technology
Position Type: Contract
Contract Rate: $75.00/hr+
Location: Chicago preferred – remote okay
? Role Overview
We are seeking an elite, highly adaptable Senior Technical Project Manager to drive critical initiatives across Infrastructure Operations, Cloud, DevOps, Architecture, and foundational AI Platform teams.
This is not a traditional scrum-master, meeting-scheduler, or note-taking role. We are looking for a heavyweight, autonomous driver who thrives in chaos. The ideal candidate can walk into highly ambiguous environments with zero established playbook, quickly build repeatable operating models from scratch, and seamlessly translate complex engineering noise into high-level business outcomes for executive leadership.
?? Key Responsibilities
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Create Order from Chaos: Walk into shifting, unstructured environments to independently build project plans, governance frameworks, accountability structures, and communication matrices.
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Bridge the Technical-Executive Gap: Attend deep-dive engineering, cloud architecture, and infrastructure sessions and translate complex technical complexities into clear executive updates, business impacts, and critical decision points.
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Drive Complex Technical Portfolios: Manage multiple concurrent, cross-functional infrastructure initiatives ranging from $1M to $5M in scale (e.g., operationalizing enterprise tools like Dynatrace, driving endpoint device refreshes, and mapping infrastructure for the foundational AI Platform).
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Navigate a Matrixed Ecosystem: Influence without authority across highly matrixed departments, collaborating closely with varied leadership styles and adapting reporting delivery to match individual leader preferences.
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Proactive Risk & Dependency Management: Own enterprise-level project fundamentals—anticipating bottlenecks, managing complex technical dependencies, and mitigating risks before they impact delivery.
? Target Candidate Profile & Qualifications
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Ambiguity Master (30%): A proven track record of entering environments with no defined process or governance and successfully building and driving adoption of new operational frameworks.
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Technical Translator (25%): Exceptional executive-level communication and storytelling skills. The ability to speak the language of engineers and architects, but write for C-suite leaders.
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Enterprise PM Fundamentals (20%): 8 to 12 years of true enterprise-scale project management experience spanning risk, stakeholder, and execution management.
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Extreme Adaptability (15%): Methodologically flexible. A professional who pivots seamlessly between teams and delivery methods, rejecting rigid “one-way” frameworks.
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Infrastructure & Cloud Fluency (10%): Direct experience managing projects within Cloud, DevOps, Enterprise Architecture, or Core Infrastructure environments. Must understand the technical ecosystem conceptually, without trying to act as the engineer.
Nice-to-Haves
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Familiarity or exposure to foundational AI Platforms/Infrastructure.
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General exposure to Dynatrace or enterprise monitoring ecosystems (expertise not required).
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PMP Certification (valued, but verified enterprise battle-scars are preferred).