Senior IT Project & Program Manager- AI Initiatives

Diversified Services Network, Inc.•Chicago, IL

1d•Remote

About The Position

Diversified Services Network, Inc. (DSN) is seeking a full-time IT Project/Program Manager-AI Initiatives to join our team in your choice of our Chicago, IL, Peoria, IL, Dallas, TX, Broomfield, CO locations! We offer a remote work model, full benefits, PTO, 401k, and more! If you're looking to grow your technical career within an extremely reputable, stable Fortune 500 company - let's talk!

Requirements

Bachelors/ Master’s degree with 5+ years’ experience
Strong working knowledge of digital project management fundamentals, including project planning, scheduling, dependency management, and critical path analysis.
Experience using project management and workflow tools to manage plans, track progress, and report status (e.g., enterprise PM or agile delivery tools).
Proven ability to manage multiple workstreams and cross‑functional dependencies within complex digital initiatives.
Solid understanding of risk and issue management practices, including escalation, mitigation planning, and stakeholder communication.
Ability to analyze project data (schedule, milestones, risks) and translate it into clear, actionable insights for teams and leaders.
Strong facilitation and communication skills to lead meetings, drive alignment, and maintain clarity across technical and non‑technical stakeholders.
Familiarity working in technology or digital delivery environments, ideally supporting software, data, or AI‑enabled solutions.
Heavy attention to detail
Organizational skills
Excellent communication skills

Nice To Haves

PMO certification or Agile Certification is nice to have

Responsibilities

Provides delivery rigor and execution leadership for AI Assistant initiatives by establishing clear plans, dependencies, and accountability across cross‑functional teams.
Creates transparency for the work group by maintaining up‑to‑date project plans, schedules, risks, and status reporting to support informed decision‑making.
Enables effective collaboration between product, engineering, data/AI, UX, and business partners by facilitating structured communication and alignment forums.
Proactively identifies delivery risks, dependency constraints, and critical path impacts, helping the team address issues early and maintain momentum.
Supports continuous improvement of project management practices, tools, and cadence to improve predictability, efficiency, and stakeholder confidence.
Develop, maintain, and regularly update integrated project plans that include workstreams, milestones, dependencies, and critical path identification.
Track progress against schedules and commitments; identify variances and drive corrective actions in partnership with delivery teams.
Lead recurring execution and governance meetings (e.g., standups, status reviews, stakeholder updates), ensuring clear agendas, decisions, and next steps.
Coordinate cross‑functional dependencies across multiple teams and time zones to ensure sequencing and handoffs are clearly understood and managed.
Identify, document, and manage project risks, issues, and assumptions; develop mitigation and contingency plans as needed.
Prepare and deliver concise project status communications, including schedule health, risks/issues, decisions required, and upcoming milestones.
Ensure project deliverables meet defined quality standards and are aligned with agreed‑upon scope, timelines, and expectations.
Maintain project documentation, action items, and decision logs to support transparency and auditability throughout the project lifecycle.