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Inspira Financial · 10 hours ago

Director, Program Management

Oak Brook, IL

Full-time

Onsite

Senior Level, Lead/Staff

$135K/yr - $160K/yr

10+ years exp

Inspira Financial is focused on helping businesses and individuals thrive in health and wealth. The Director of Program Management will lead large, cross-functional programs that drive platform transformation and growth initiatives, ensuring measurable outcomes in alignment with the company's business strategy.

Financial Services

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

Qualification

Program managementFinancial services experienceHealthcare benefits knowledgeAgile delivery modelsEnterprise governanceRisk managementFinancial modelingStakeholder managementAnalytical skillsChange managementPortfolio prioritizationAI tools proficiencySalesforce familiarityJira familiaritySmartsheet familiarityProblem-solving skillsCommunication skillsTeam leadershipCollaboration skills

Required

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

Preferred

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