Senior AI Technical Project Manager

Reuben Cooley Inc.; Chicago (IL); On-site; USD 140,000 - 190,000; Full time

Job summary

Reuben Cooley Inc. is seeking an experienced AI Technical Project Manager to lead delivery and portfolio governance of Generative AI, AI/ML, and AWS-based solutions. You will oversee multiple AI initiatives and provide consolidated updates to senior leadership.

In this role you will drive end-to-end execution, manage a cross-functional team, own Agile ceremonies, and ensure on-time, within-scope delivery while communicating risks and status to executives.

Qualifications

• 10+ years of technical project or program management experience.
• Proven delivery of AWS-based AI/ML and Generative AI projects.
• Strong communication and stakeholder management skills.

Responsibilities

• Own end-to-end delivery of GenAI and AI/ML projects from planning through production deployment.
• Manage a portfolio of AI initiatives with consolidated dashboards, executive reports, and program health updates.
• Coordinate with project managers, architects, data scientists, engineers, and business stakeholders to ensure successful delivery.
• Lead all Agile/Scrum ceremonies, including Sprint Planning, Daily Stand-ups, Backlog Grooming, Sprint Reviews, Demos, and Retrospectives.
• Track project scope, timelines, budgets, dependencies, risks, and deliverables.
• Proactively identify risks, develop mitigation plans, manage escalations, and remove delivery roadblocks.
• Drive stakeholder communication, executive updates, governance reviews, and leadership presentations.
• Manage cross-project dependencies, resource conflicts, and portfolio-level priorities.

Skills

Technical PM

AWS AI/ML

Generative AI

Agile/Scrum

Stakeholder mgmt

Jira/Confluence

Tools

Jira

Confluence

Azure DevOps

Microsoft Project

Smartsheet

Job description

We are seeking an experienced AI Technical Project Manager to lead the delivery and portfolio governance of Generative AI, AI/ML, and AWS-based solutions. This role will oversee multiple AI initiatives, drive end-to-end project execution, and provide consolidated portfolio updates to senior leadership

Key Responsibilities

• Own and lead end-to-end delivery of GenAI and AI/ML projects from planning through production deployment.


• Manage a portfolio of AI initiatives, creating consolidated dashboards, executive reports, and program health updates.


• Coordinate with project managers, architects, data scientists, engineers, and business stakeholders to ensure successful delivery.


• Lead all Agile/Scrum ceremonies, including Sprint Planning, Daily Stand-ups, Backlog Grooming, Sprint Reviews, Demos, and Retrospectives.


• Track project scope, timelines, budgets, dependencies, risks, and deliverables.


• Proactively identify risks, develop mitigation plans, manage escalations, and remove delivery roadblocks.


• Drive stakeholder communication, executive updates, governance reviews, and leadership presentations.


• Manage cross-project dependencies, resource conflicts, and portfolio-level priorities.

Required Qualifications

• 10+ years of Technical Project Management, Program Management, or Delivery Leadership experience.


• Proven experience delivering AWS-based AI/ML and Generative AI projects.


• Good understanding of:


• Generative AI, LLMs, RAG, AI Agents, Prompt Engineering


• Machine Learning Lifecycle


• MLOps / LLMOps concepts


• AWS AI services such as Bedrock, SageMaker, Lambda, S3, OpenSearch, etc.


• Experience managing multiple concurrent projects and providing portfolio-level governance.


• Strong expertise in Agile/Scrum methodologies and facilitation of all Scrum ceremonies.


• Hands-on experience with Jira, Confluence, Azure DevOps, Microsoft Project, Smartsheet, or similar project management tools.


• Excellent communication, executive presentation, stakeholder management, and leadership skills.


• Strong risk management, planning, prioritization, and problem-solving abilities.

Preferred Qualifications

• PMP, PMI-ACP, Certified Scrum Master, or SAFe certification.


• AWS Cloud or Machine Learning certifications.


• Experience in consulting, digital transformation, or customer-facing AI program.

Ideal Candidate

A strategic AI delivery leader who can effectively engage with business executives, technical teams, product leaders, and project managers while driving successful execution of multiple AI initiatives. The individual should be capable of providing portfolio-level oversight, proactive risk management, executive reporting, and predictable delivery of enterprise GenAI and AI/ML programs.

Need folks who discuss projects with CXO/stakeholders and not delivery team