Director, Program Management

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. 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? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
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
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.
Duties & 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.

People Leader Responsibilities:

• 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.

Preferred Qualifications
Education & Experience:

• 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
• 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.

Skills & Abilities:

• 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.

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 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

Compensation & Benefits
$135,000-$160,000 per year