Project/Program Manager IT

Senior IT Project Manager

Application Development | Cross-Functional Alignment | Executive Reporting

Full-Time | Hybrid (3 Days On-Site) | 5+ Years Experience

Diversified Services Network, Inc. (DSN) is seeking a full-time Senior IT Project Manager to join our team in Chicago, IL! We offer full benefits, PTO, 401k, and more! If you are a high-impact project manager who excels at synthesizing complex, cross-team inputs into structured, decision-ready insights and thrives in fast-paced, matrixed environments within an extremely reputable, stable Fortune 500 company — let’s talk!

Position Overview

We are seeking a Senior IT Project Manager to drive clarity, alignment, and execution visibility across application development initiatives within our digital organization, in a hybrid role based in Chicago, IL (3 days on-site per week). This role partners closely with Engineering, Product, Platform, and Analytics teams to ensure leadership has a consistent, clear view of progress, risks, and priorities. You will synthesize complex, cross-team inputs into structured, decision-ready narratives and professional reporting for a variety of audiences — from development teams to senior leadership.

The ideal candidate brings strong executive presence, structured thinking, and a talent for distilling ambiguity into clear takeaways.

Key Contributions & Responsibilities

• Serve as the primary communicator for division development — attend development and technical meetings to elicit timelines, issues, and risks, and translate them into cohesive development narratives highlighting milestones, delays, and challenges.

• Create professional, audience-tailored slide decks and reports that clearly illustrate relevant status, risks, and priorities for development teams, product owners, and senior leadership.

• Own roadmap management — maintain a clear, current view of delivery commitments, milestones, and sequencing across cross-functional teams.

• Track risks and dependencies across Engineering, Product, Platform, and Analytics; drive follow-up actions and escalate blockers to ensure delivery stays on schedule.

• Drive cross-functional alignment — ensure teams are coordinated on priorities, dependencies, and accountability in a matrixed organization.

• Operate independently with strong judgment, setting priorities and managing a broadly defined workload with minimal oversight.

Team Structure & Work Environment

• You will interact regularly with development teams, product owners, and senior staff across the digital organization, serving as a connective layer across multiple disciplines and leadership levels.

• This is a hybrid role requiring 3 days on-site per week in Chicago, IL.

Requirements

Candidate Requirements

Education & Experience

• Bachelor’s degree required with 5+ years of relevant project management experience. MBA or equivalent business training preferred.

• Experience working in software development organizations is required.

Required Technical Skills

• Microsoft Office Suite proficiency, with particular strength in PowerPoint (executive-level deck creation) and Excel.

• Azure DevOps — for tracking work items, managing delivery artifacts, and maintaining project visibility.

• Understanding of SDLC and CI/CD concepts sufficient to engage meaningfully with engineering teams and accurately capture delivery status.

• Power BI — for data visualization and reporting to support delivery insights and stakeholder communication.

• SQL and/or Python — for querying and analyzing delivery data to support structured reporting and storytelling.

Required Soft Skills

• Executive presence — confident engaging with senior leadership and able to tailor content and communication style to different audiences.

• Structured thinking and strong storytelling through data — able to distill ambiguity and complex cross-team inputs into clear, decision-ready takeaways.

• High attention to detail — ensures accuracy and consistency across all reporting, slide decks, and delivery tracking artifacts.

• Ability to operate independently with strong judgment in a fast-paced, matrixed environment.

Benefits

• 401(k)

• Dental insurance
• Vision Insurance
• Disability insurance
• Employee assistance program
• Health insurance
• Health savings account
• Life insurance
• Paid time off
• Paid Holidays

Please follow the link to our website for a list of job openings in Engineering, IT, Project Management, and more!

Salary expectations: 90,000-107,000 per annual