Inspira FinancialTake 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.
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 Sr. Director, Platform Migration & Enterprise Program Management will serve as the single accountable leader for Inspira Financial's multi-year platform migration and modernization roadmap across the Health & Benefits portfolio.
This role owns end-to-end orchestration of one of the company's most critical strategic initiatives, ensuring disciplined execution, strong governance, and measurable business outcomes over multiple years.
This leader will operate as a autonomous executive, bridging strategy and execution across Product, Technology, Operations, Sales, Client Success, and external partners.
The role requires deep experience leading large-scale platform migrations, enterprise transformations, and complex dependency-driven programs, with credibility at the executive and board-level.
Reporting to the Managing Director of Business Transformation, this position will act as a trusted advisor to senior leadership, shaping delivery strategy, sequencing, investment decisions, and organizational readiness throughout the migration journey.
Own the end-to-end delivery of Inspira's multi-year platform migration strategy, serving as the primary executive owner for scope, sequencing, risk, and outcomes.
Translate enterprise strategy into an integrated migration roadmap, managing interdependencies across legacy platforms, new technology, operations, and client transitions.
Ensure platform migration activities are aligned to growth strategy, client experience goals, regulatory requirements, and financial targets.
Establish and lead a best-in-class enterprise PMO operating model for platform migration and transformation initiatives.
Define governance structures, decision forums, escalation paths, and success metrics to ensure predictable, transparent execution.
Drive portfolio prioritization, capacity planning, and funding alignment across concurrent initiatives.
Serve as the final escalation point for delivery risks, trade-off decisions, and cross-functional conflicts.
Act as a strategic partner to executive leaders across Product, Technology, Operations, Sales, Finance, Risk, and Compliance.
Prepare and deliver concise, data-driven executive communications on progress, risks, financials, and mitigation plans.
Build strong working relationships with external vendors, implementation partners, and technology providers, holding them accountable to outcomes.
Own business case development, multi-year investment planning, and ROI tracking for platform migration initiatives.
Partner with Finance to manage budgets, forecast spend, and ensure value realization over time.
Continuously evaluate cost, benefit, and risk trade-offs to maximize enterprise return.
Partner with leaders across the organization to ensure operational readiness, change management, and adoption are embedded into migration plans.
Champion a "one-enterprise" mindset, aligning teams around common goals, milestones, and delivery standards.
Ensure client experience, service continuity, and regulatory obligations remain uncompromised throughout transition phases.
Build, mentor, and scale a high-performing program and project leadership bench.
Set clear expectations, operating rhythms, and performance standards for program teams.
Model disciplined execution, accountability, collaboration, and adaptability across the organization.
Education & Experience
12+ years of experience leading enterprise-scale programs, portfolios, or Transformations.
7+ years in senior leadership roles with accountability for cross-functional delivery.
Proven success leading large, multi-year platform migrations or enterprise technology transformations.
Strong background in financial services, healthcare benefits, fintech, or regulated industries.
Demonstrated expertise in PMO leadership, enterprise governance, and portfolio management.
Experience working with Agile, hybrid, and traditional delivery models at enterprise scale.
Bachelor's degree required; Master's degree (MBA, MS, or equivalent) preferred.
Skills & Abilities
Enterprise-level strategic thinking with the ability to translate vision into executable roadmaps
Exceptional executive presence and C-suite communication skills
Deep understanding of program governance, dependency management, and risk mitigation
Strong financial acumen, including budget ownership, forecasting, and ROI tracking
Advanced problem-solving skills with comfort navigating ambiguity and complexity
Fluency with AI-enabled productivity, analytics, and delivery tools
Experience with enterprise platforms and tools such as Salesforce, Jira, Smartsheet, and portfolio management solutions
$225,000-$235,000 per year
$225,000-$235,000 per year
Compensation & Benefits The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities.
Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.
Compensation & Benefits The compensation for this position will vary depending on factors such as your location, skills and experience. The compensation package may also include incentive and bonus opportunities.
Inspira provides industry-leading benefits including, but not limited to: healthcare, 401K savings plan, company holidays, paid time off, parental leave and an employee assistance program.
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