Director Program Management

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.

What We Do

Inspira Financial provides health wealth retirement and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients representing over $62 billion in assets Inspira works with thousands of employers plan sponsors recordkeepers TPAs and other institutional partners — helping the people they care about plan save and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services health savings accounts emergency savings funds custody services and more. Learn more at inspirafinancial.com.

Why Work With Us

Inspira Financial is a leading financial services company offering specialized financial wellness solutions to employers institutions advisors and individuals.

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