Director Program Management Jobs in Illinois (NOW HIRING)

The Director, Program Management Office (PMO) is a senior delivery leader responsible for building and operating Inspira Financial's Health & Benefits (H&B) project portfolio management capability. Reporting to the Senior Director, Program Management within the Execution Office, this role owns the end-to-end intake, prioritization, resourcing, and execution management of Inspira's highest-priority initiatives across Health & Benefits, Service Delivery, and Technology.

The Director leads a team of Program Managers, Senior Project Managers, and Project Managers, ensuring that Health & Benefits (H&B) projects are governed effectively, delivered on time and within scope, and aligned to Inspira's strategic OKRs. This role is distinct from the Center of Excellence (CoE) function: the Director, PMO is accountable for portfolio execution and delivery performance, not for process documentation, template maintenance, or PM training - those responsibilities sit with the Process & Tools Manager (CoE Lead).

Duties & Responsibilities:

Portfolio Management & Intake

• Own the Health & Benefits (H&B) project intake process: receive, evaluate, and triage incoming project requests from business leaders, ensuring all submissions are properly scoped and assessed against strategic fit and capacity.
• Maintain a consolidated, real-time portfolio view of all active and queued Health & Benefits (H&B) initiatives, inclusive of status, resource allocation, dependencies, and risk posture.
• Lead the portfolio prioritization process in partnership with the Senior Director and executive stakeholders, sequencing initiatives against organizational capacity, strategic importance, and budget.
• Identify and actively manage cross-initiative dependencies, sequencing conflicts, and capacity bottlenecks before they become delivery risks.

Delivery Execution & Governance

• Deploy and manage Program Managers, Senior Project Managers, and Project Managers to Health & Benefits (H&B) initiatives based on project complexity, scope, and skill requirements.
• Establish and enforce project governance standards: proper use of charters, tollgates, RACI frameworks, risk registers, and milestone-based reporting across all PMO-managed projects.
• Serve as the primary escalation point for delivery risks, scope changes, budget variances, and cross-functional blockers, coordinating resolution across business and technology stakeholders.
• Ensure all PMO-managed projects adhere to the frameworks and toolkits developed by the CoE; partner with the Process & Tools Manager to identify gaps and improvements.
• Drive adoption of the Health & Benefits (H&B) PPM tool for all active projects, ensuring data integrity for executive portfolio reporting.

Executive Reporting & Stakeholder Management

• Prepare and deliver concise, data-rich portfolio dashboards and executive updates to the Senior Director and C-suite, surfacing delivery health, risk posture, and capacity trends.
• Build and maintain trusted relationships with senior business leaders, executive sponsors, and external partners across the Health & Benefits (H&B).
• Translate organizational strategy into actionable delivery roadmaps, communicating trade-offs and sequencing decisions with clarity and confidence.
• Facilitate alignment sessions and steering committee meetings, ensuring decision-making momentum on critical in-flight programs.

Team Leadership & Talent Development

• Lead, coach, and develop a team of Program Managers, Senior Project Managers, and Project Managers - setting clear performance expectations, providing regular feedback, and building career growth plans.
• Partner with the Senior Director and CoE to ensure all PMO team members are trained on and consistently apply Health & Benefits (H&B) delivery standards and toolkits.
• Oversee hiring, onboarding, and performance management for all PMO direct reports.
• Identify skill gaps within the PMO team and work with HR and the CoE to close them through targeted development or hiring.
• Model a culture of accountability, transparency, and continuous improvement within the PMO.

Education & Experience:

• 10+ years of experience in program or portfolio management, with a minimum of 5 years in a senior leadership or cross-functional delivery role required.
• Demonstrated experience managing Health & Benefits (H&B) project portfolios with 10+ concurrent initiatives across multiple business functions.
• Background in financial services, healthcare benefits, fintech, or a similarly regulated industry strongly preferred.
• Bachelor's degree in Business, Technology, or a related field required; Master's degree (MBA or equivalent) preferred.
• PMP, PgMP, or equivalent project/program management certification strongly preferred.

Skills & Abilities:

• Proven track record of building and scaling a PMO or delivery function from the ground up, including intake processes, governance structures, and resource models.
• Expert-level portfolio management skills: capacity planning, dependency mapping, prioritization frameworks, and portfolio health reporting.
• Exceptional executive communication skills - able to synthesize complex delivery information into crisp, decision-ready narratives for C-suite audiences.
• Deep knowledge of project governance: tollgate models, risk registers, RACI, change management, and escalation frameworks.
• Proficient in Health & Benefits (H&B) PPM tools (e.g., Smartsheet, Planview, Jira, Microsoft Project); experience leading PPM tool selection or implementation a plus.
• Strong financial acumen: experience managing project budgets, developing business cases, and tracking delivery ROI.
• Experienced in Agile, waterfall, and hybrid delivery models with the judgment to apply the right approach by initiative type.
• Fluency with AI-powered productivity, analytics, and collaboration tools; able to leverage artificial intelligence to drive portfolio efficiency and data-driven decision-making.
• Strong analytical and problem-solving orientation with a bias for action and a record of removing blockers at pace.

Other Requirements:

• Typical schedule is Monday-Friday, 8 am to 5 pm CT; ability to work evening/weekend hours may be required during peak periods.
• Employees within a 90-minute radius of the Oak Brook, IL headquarters, are required to adhere to Company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm CT (1 of the 4 days must be a Monday or Friday).
• Occasional travel up to 25%.
• Ability to provide personal transportation for training or meetings may be required.
• Occasionally lifts up to 25 pounds; prolonged periods of sitting and operating standard office equipment.