Director Program Management

Join Us!
Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.
Our values shape how we show up every day. We Lead with Heart by acting with compassion, empathy, and doing what's right; Cultivate Trust through integrity, transparency, and accountability; Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.
Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life-changing impact that enriches lives and helps build a better future. Learn more at inspirafinancial.com.
We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday). This requirement does not apply to support specialist positions.
Don't meet every single requirement? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey. We look forward to receiving your application.
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 .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
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.

Preferred Qualifications
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.

Compensation & Benefits
$160,000-$175,000 per year