Director, Program Management

Inspira Financial•Oak Brook, IL

59d•Hybrid

About The Position

Director, Program Management will report to the Managing Director, Business Transformation. The Director will lead large, cross-functional programs that drive Inspira Financial’s platform transformation and growth initiatives across the Health & Benefits portfolio. This role is responsible for orchestrating delivery across multiple workstreams—including product, technology, operations, and client success—to ensure complex initiatives deliver measurable outcomes in alignment with our business strategy. This role combines program execution discipline with strategic insight.

Requirements

10+ years of experience in program or portfolio management, with at least 5 years in a leadership or cross-functional delivery role required
Background in financial services, healthcare benefits, or fintech required.
Bachelor’s degree in business, technology or related, or equivalent combination of education, experience and training required
Proven success managing enterprise-scale transformations or technology implementations
Experience with Agile or hybrid delivery models, enterprise governance, and risk management
Exceptional strategic and operational thinking—able to connect long-term vision to actionable execution.
Fluency with AI-powered productivity, analytics, and collaboration tools; able to leverage artificial intelligence to drive program efficiency, data-driven decision-making, and innovation.
Demonstrated executive communication and stakeholder management skills across all organizational levels.
Proficient in financial modeling, forecasting, and reporting to track ROI and performance metrics.
Strong analytical and problem-solving skills with a bias for action and results.
Deep understanding of program governance, change management, and portfolio prioritization frameworks.
Familiarity with Salesforce, Smartsheet, Jira, and other enterprise planning tools.
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 our 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

Nice To Haves

Master’s degree preferred
The ideal candidate will possess strong business acumen, deep understanding of financial and health benefits ecosystems, and the ability to build trust-based relationships with executive stakeholders, external partners, and internal delivery teams.

Responsibilities

Own strategic execution of cross-enterprise programs that support Inspira’s growth strategy and platform modernization efforts.
Establish program governance, structure, and success metrics to ensure on-time, on-budget, and high-quality delivery.
Partner with Product, Technology, Sales, and Operations leaders to define scope, prioritize workstreams, and align resources to achieve strategic objectives.
Translate strategy into actionable roadmaps, managing dependencies across multiple programs and identifying critical path items.
Bring the voice of the customer and data-backed insight into all program decisions to improve experience, efficiency, and scalability.
Develop business cases and financial tracking models to monitor ROI, manage budgets, and ensure fiscal accountabilities for all programs under management.
Act as an escalation and resolution point, coordinating across departments to remove roadblocks and maintain momentum.
Communicate effectively with executive leadership, preparing concise and data-rich updates on progress, risks, and mitigation plans.
Provide clear direction and measurable objectives to program and project teams.
Serve as a trusted advisor to senior leadership on program strategy, portfolio prioritization, and organizational readiness.Model collaboration, adaptability, results orientation, bridging business strategy and operational execution.Foster cross-departmental alignment, creating one unified delivery approach across Product, Operations, and Technology.
Other duties as assigned.
Manages a team of 2 directs to achieve results.
Develops and mentors talent—building Inspira’s next generation of delivery leaders through consistent coaching and development planning.
Provides regular and timely feedback, sets performance goals, and supports professional growth.
Oversees hiring and training processes to cultivate a high-performing team.
Directs the daily workflow of the team/department.