Director, Strategic Portfolio Management

At the Federal Home Loan Bank of Chicago, employees come first - that’s why we offer a highly competitive compensation and bonus package, and access to a comprehensive benefits program designed to meet the needs of our employees.   C ollaborative, in-office operating model Retirement program (401k and Pension)   Medical, dental and vision insurance   Lifestyle Spending Account   Competitive PTO plan   11 paid holidays per year ​ Who we are Our mission at FHLBank Chicago: To partner with our members in Illinois and Wisconsin to provide them competitively priced funding, a reasonable return on their investment, and support for their community investment activities. Simply said, we're a bank for banks and other financial institutions, focused on being a strategic partner for our members and working together to reinvest in our communities, from urban centers to rural areas. Created by Congress in 1932, FHLBank Chicago is one of 11 Federal Home Loan Banks, government sponsored in support of mortgage lending and community investment. What it’s like to work here At FHLBank Chicago, we bring people together. We are committed to a high performing, engaged workforce, and to supporting the communities we serve across Illinois and Wisconsin. Our Buddy Program pairs new hires with tenured employees to guide their onboarding. Our professional development and training opportunities through upskilling, mentorship programs, and tuition reimbursement allow employees to grow their career with us. Our collaborative, in-office operating model brings teams together to foster innovation, connection, and shared success. To support balance and flexibility, employees are provided an allocation of remote days to use as needed throughout the year. What you’ll do: The Director of Strategic Portfolio Management is responsible for leading the enterprise technology intake, prioritizations, governance, and portfolio management function. This role partners closely with business and technology leaders to ensure technology investments align with strategic priorities, deliver measurable business value, and optimize organizational capacity. This leader oversees the end-to-end intake and evaluation process for new technology initiatives, guiding teams through business case development, value articulation, high-level estimation, and prioritization. The role also facilitates executive governance through the Initiative Oversight Committee (IOC), serving as a strategic advisor in prioritization, sequencing, funding, and trade-off discussions. Reporting into the Senior Managing Director, Technology Transformation & Governance, this role leads a team responsible for intake and prioritization, resource and capacity planning, portfolio analytics and reporting, and program/project management How you’ll make an impact: Drive strategic investment decisions that maximize business value and ensure IT resources are focused on the initiatives with the greatest impact Create a disciplined portfolio management capability that brings transparency, consistency, and data-driven decision making to technology investments Partner with executive leadership to proactively identify portfolio risks, resource constraints, and delivery trade-offs, enabling more predictable execution of strategic investments What you can expect: Portfolio Governance & Prioritization Lead enterprise technology portfolio governance processes, including intake, evaluation, prioritization, and sequencing of initiatives Facilitate the Initiatives Oversight Committee (IOC), enabling effective execution decision-making and trade-off discussions Drive transparent prioritization frameworks aligned to strategic goals, capacity constraints, and investment objectives Partner with executive leadership to assess impacts of new work requests on existing strategic commitments Establish governance standards, portfolio rhythms, and decision frameworks across the PMO Intake & Business Case Development Oversee intake processes for technology initiatives, ensuring requests are properly documented, evaluated, and aligned to enterprise priorities Guide business and technology teams through development of business cases, value assessments, benefit realization assumptions, and high-level delivery estimates Ensure initiatives include clear strategic alignment, expected outcomes, dependencies, and resource impacts Drive consistency and quality in intake artifacts and governance readiness Portfolio Planning & Capacity Management Lead enterprise portfolio planning actiities, including quarterly and annual planning cycles Partner with technology and business leaders to maintain visibility into organizational capacity, resource constraints, and delivery demand Support prioritization and sequencing decisions through resource and capacity analysis Identify portfolio risks, dependencies, and delivery conflicts across strategic initiatives Reporting & Portfolio Analytics Oversee portfolio health reporting, executive dashboards, KPIs, and strategic initiative metrics Delivery actionable insights and analytics to support executive decision-making Establish portfolio measurement standards, including delivery performance, throughput, capacity utilization, and value realization metrics Drive continuous improvement in portfolio transparendcy and reporting capabilities Leadership & Team Management Lead and develop a portfolio management team including: Intake & Proiritization Lead Resource & Capacity Planner Portfolio Data Analytics Lead Program & Project Managers Foster a culture of collaboration, accountability, continous improvement, and strategic partnership Build strong relationships across business, techhology, finance, and executive leadership teams What you’ll bring: 15+ years experience in portfolio management, PMO leadership, technology governance, or strategic planning 5+ years of leadership experience 4 year Bachelor’s