Senior Digital Program Manager

Jobtailor; Chicago (IL); On-site; USD 110,000 - 140,000; Full time

Job summary

Jobtailor in Chicago, IL seeks a seasoned Digital Project Manager to coordinate large-scale programs, chartering, governance, and benefits realization. You will guide cross-functional teams, manage dependencies, and communicate status to clients and stakeholders using cloud-based platforms and modern delivery practices.

The role requires 5+ years in Agile project management, experience delivering AI programs, and strong know-how of MS Azure DevOps, Power BI, and Confluence.

Qualifications

• Bachelor’s or Master’s degree with 5+ years of experience in program/PM roles.

Responsibilities

• Lead planning and execution of program deliverables and ensure alignment with business objectives.
• Highlight dependencies between projects and manage cross-functional team execution.
• Serve as principal communicator with clients and internal stakeholders on program status and risks.
• Identify and mitigate risks and issues with timely actions.
• Define program scope and success metrics to realize benefits within defined timeframes.

Skills

Agile Project Management

Program Management

Stakeholder Communication

Risk Management

Leadership

Mentorship

Problem Solving

Cross-functional Collaboration

Education

Bachelor’s degree in Information Systems, Computer Science, or related field

Master’s degree

Tools

MS Azure DevOps

Power BI

Confluence

Job description

• Manage planning and execution of project deliverables, including the project charter, communications, metrics, reporting, and overall program plan
• Highlight dependencies between projects under the same program
• Guide cross-functional teams in project execution using cloud-based platforms, digital processes, and business acumen
• Manage multiple projects concurrently
• Apply knowledge of internal systems, processes, procedures, competitors, laws, regulations, and market conditions
• Serve as principal communicator with clients and internal stakeholders regarding project status
• Identify and manage risks and issues and take timely mitigation action
• Define program scope and success indicators to realize program benefits within a defined timeframe
• Apply Agile or Waterfall program management methodologies and current industry practices such as DevOps and Continuous Integration/Continuous Delivery
• Prioritize program requirements with the Product Owner and stakeholders
• Develop communication and stakeholder management plans, including stakeholder register and analysis
• Provide regular updates to business stakeholders and consumers of program deliverables
• Create and manage dependencies across active projects and collaborate across the program
• Evaluate program team members and identify opportunities to add or train resources
• Provide leadership and mentorship to less experienced Digital Project Managers
• Develop the program budget, track actuals, and complete quarterly spend forecasts
• Communicate program status using a visual reporting tool and maintain program artifacts, including lessons learned
• Advocate for the digital program and support successful adoption
• Collaborate with global, cross-functional teams

Requirements

• Bachelor’s degree in Information Systems, Computer Science, or a related field, and 5+ years of professional experience in this capacity OR Master’s degree with 5+ years of experience
• Experience working with large programs or enterprise organizations
• Familiarity and prior experience leading cross‑organizational system testing teams
• 5+ years of experience with Agile project management
• Experience delivering AI programs
• Technical education/background in development engineering management
• Knowledge of MS Azure DevOps, Power BI, and Confluence
• Experience managing software development projects/programs in large matrix organizations
• Advanced human relations skills for a cooperative working relationship with others inside and outside the department
• Ability to drive issues to resolution
• Excellent communication skills with the ability to engage with all levels of the organization

Core Competencies

Demonstrates expertise in managing complex projects using Agile and Waterfall methodologies, with a strong focus on stakeholder communication, risk management, and program execution. Proficient in leveraging cloud-based platforms and tools like MS Azure DevOps and Power BI to drive project success and collaboration across cross‑functional teams.

Highest-signal resume keywords

• Agile Project Management
• Program Management
• MS Azure DevOps
• Stakeholder Communication
• Risk Management

Hard Skills

• Project Management
• Program Scope Definition
• Metrics Reporting
• Digital Processes
• AI Program Delivery
• Software Development Management
• System Testing Leadership
• Budget Development
• Continuous Integration/Continuous Delivery
• DevOps Methodology

Soft Skills

• Excellent Communication Skills
• Advanced Human Relations Skills
• Leadership
• Mentorship
• Problem Solving

Industry Keywords

• Enterprise Organizations
• Cross‑Functional Teams
• Project Dependencies
• Market Conditions
• Internal Systems Knowledge

Tools & Technologies

• Power BI
• Confluence
• Cloud-Based Platforms
• Visual Reporting Tools