IT Senior Program Manager

Paradigm•Lombard, IL

1d•Remote

About The Position

We are seeking a full-time, remote IT Program Manager. The IT Program Manager will be responsible for leading and developing a team of project managers, establishing clear roles and processes, and ensuring disciplined delivery of complex, cross-functional programs. They play a key role in shaping Paradigm’s project management framework, driving strategic direction, and fostering a culture of accountability, innovation, and continuous improvement. RESPONSIBILITIES: Strategic Direction & Role Clarity Define, communicate, and enforce clear roles and responsibilities for project managers, supporting Paradigm’s transition to a structured, process-driven framework. Mentor, train, and supervise project managers, providing effective feedback and fostering a high-performance team culture. Guide, maintain, and enforce departmental practices, methodologies, policies, and procedures. Scope Management & Timeboxed Releases Lead the team in planning high-level features and scope items for timeboxed releases, ensuring incremental and predictable delivery. Coordinate with internal stakeholders to understand business goals and objectives, translating them into actionable directives for project managers interacting with digital product teams and business analysts. Maintain situational awareness and a keen sense of urgency in responding to digital product, business, and IT environmental influences. Governance, Reporting & Resource Management Implement robust governance standards, including RAID logs, risk management, and mitigation planning. Oversee status tracking, resource prioritization, and schedule adherence for all programs. Establish and track IT implementation metrics (KPIs) and team dashboards to increase visibility, alignment, and accountability. Produce regular, comprehensive reporting on project/program status, budgets, schedules, resource allocation, and operational effectiveness for the Steering Committee and leadership team. Quality Assurance & Deployment Discipline Champion disciplined QA/UAT and deployment processes, ensuring accuracy in project management tools and timely communication of deployment readiness. Support the team in developing and maintaining project milestones, work breakdown structures, and contingency plans. Ensure successful implementation within defined timeframes and budgets. Innovation & AI Enablement Drive adoption of AI tools (e.g., Microsoft 365 Copilot) to enhance project management efficiency, automate status summaries, risk registers, and weekly updates. Work with App Dev Directors and digital product owners on continuous improvements of technology capabilities to ensure efficient and effective implementations. Provide strategic insights to organizational leaders on process improvements that reduce time to market, lower costs, and increase ROI. Stakeholder Engagement & Communication Maintain communication with digital product management and internal stakeholders on overall project status, milestones, and risks. Create and maintain standard operating process reference material for internal staff and digital product management, including workflows and solution delivery protocols. Demonstrate outstanding communication and presentation skills, conveying sophisticated concepts simply and clearly to a variety of audiences.

Requirements

Bachelor’s Degree in Computer Science, Project Management, Business Management, or related field, or equivalent experience.
8-10 years of program/portfolio planning and management experience.
15+ years of direct IT project management experience, including managing multiple projects and leading project managers.
PMP or PMP-ACP certification required.
Demonstrated experience leading strategic technology initiatives.
Proven expertise in project governance, risk management, change management, and people management.
Strong business/digital product management engagement, communication, and organizational skills.
High proficiency with project management tools (e.g., MS Project, Planview), Microsoft productivity tools, and MS Office suite.
Strong business analysis and IT integration skills.
Strong IT Agile experience.

Nice To Haves

Working knowledge of the Workers’ Comp industry is a plus.

Responsibilities

Define, communicate, and enforce clear roles and responsibilities for project managers, supporting Paradigm’s transition to a structured, process-driven framework.
Mentor, train, and supervise project managers, providing effective feedback and fostering a high-performance team culture.
Guide, maintain, and enforce departmental practices, methodologies, policies, and procedures.
Lead the team in planning high-level features and scope items for timeboxed releases, ensuring incremental and predictable delivery.
Coordinate with internal stakeholders to understand business goals and objectives, translating them into actionable directives for project managers interacting with digital product teams and business analysts.
Maintain situational awareness and a keen sense of urgency in responding to digital product, business, and IT environmental influences.
Implement robust governance standards, including RAID logs, risk management, and mitigation planning.
Oversee status tracking, resource prioritization, and schedule adherence for all programs.
Establish and track IT implementation metrics (KPIs) and team dashboards to increase visibility, alignment, and accountability.
Produce regular, comprehensive reporting on project/program status, budgets, schedules, resource allocation, and operational effectiveness for the Steering Committee and leadership team.
Champion disciplined QA/UAT and deployment processes, ensuring accuracy in project management tools and timely communication of deployment readiness.
Support the team in developing and maintaining project milestones, work breakdown structures, and contingency plans.
Ensure successful implementation within defined timeframes and budgets.
Drive adoption of AI tools (e.g., Microsoft 365 Copilot) to enhance project management efficiency, automate status summaries, risk registers, and weekly updates.
Work with App Dev Directors and digital product owners on continuous improvements of technology capabilities to ensure efficient and effective implementations.
Provide strategic insights to organizational leaders on process improvements that reduce time to market, lower costs, and increase ROI.
Maintain communication with digital product management and internal stakeholders on overall project status, milestones, and risks.
Create and maintain standard operating process reference material for internal staff and digital product management, including workflows and solution delivery protocols.
Demonstrate outstanding communication and presentation skills, conveying sophisticated concepts simply and clearly to a variety of audiences.
Mentor, train, and supervise team members directly and indirectly, review their work and provide effective constructive feedback to achieve their best performance and goal attainment
Set the tone for a strong Enterprise culture and high employee engagement.
Ensure all team members understand, are trained in, and comply with Paradigm’s security requirements and policies.
Ensure all team members have the minimum level of IT system access required to effectively complete their Paradigm responsibilities.