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Sr. Manager, PMO & AI Initiatives

project44

project44

Software Engineering, Data Science
Chicago, IL, USA
Posted on Sep 17, 2025

About project44

At project44, we’re on a mission to make supply chains work. As the leading supply chain visibility platform, we provide real-time insights that empower the world’s leading brands to deliver to their customers with greater speed, efficiency, and trust.

As we continue to scale, we are looking for a Sr. Manager, PMO & AI Initiatives to oversee enterprise-wide programs and drive the successful adoption of AI across our organization. This role will sit at the intersection of strategy, operations, and innovation—ensuring we deliver business-critical projects on time while advancing AI-driven capabilities that fuel our next phase of growth.

What you’ll be working on

As Sr. Manager, PMO & AI Initiatives, you will own the planning, governance, and execution of cross-functional programs. You will partner with executives, product leaders, engineers, and data teams to ensure alignment and measurable outcomes.

You will:

  • Establish and lead a Project Management Office (PMO) to provide structure, governance, and best practices across major company initiatives.
  • Drive program planning, resourcing, timelines, and delivery for strategic initiatives spanning multiple functions.
  • Lead AI initiatives by identifying high-impact opportunities, coordinating cross-team pilots, and ensuring adoption across business units.
  • Partner with Product and Engineering to integrate AI into our marketing platform, while also enabling internal teams to leverage AI for productivity and decision-making.
  • Build dashboards, scorecards, and reporting to track progress, risks, dependencies, and ROI of enterprise programs.
  • Create executive-level updates that clearly communicate progress, blockers, and recommendations.
  • Foster a culture of accountability, transparency, and continuous improvement across all initiatives.
  • Manage change management efforts to ensure smooth adoption of new technologies, tools, and processes.

Requirements & preferred skills

  • 8+ years of experience in program management, PMO leadership, or strategic operations, ideally within SaaS, enterprise technology, or supply chain/logistics.
  • Proven track record of successfully leading cross-functional programs from strategy to execution.
  • Hands-on experience with AI/ML initiatives, either in product development or business operations.
  • Strong understanding of project management methodologies (Agile, Waterfall, or hybrid approaches).
  • Exceptional communication and stakeholder management skills; able to influence executives and cross-functional leaders.
  • Experience building and scaling PMO processes, tools, and governance models.
  • Analytical mindset, with comfort in using data to measure success, optimize execution, and drive adoption.
  • Passion for innovation and ability to translate emerging technologies into business impact.

What success looks like

  • Enterprise programs are delivered on time, on budget, and with measurable business outcomes.
  • project44 builds scalable PMO practices that provide clarity, consistency, and accountability across teams.
  • AI initiatives drive meaningful impact across product innovation, internal operations, and customer value.
  • Executive leadership has clear visibility into priorities, progress, and results.