Director, Strategic Portfolio Management

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 degree or higher in Business, Information Technoloyg, or related field
• Experience facilitating executive governance forums and prioritization discussions
• Strong understanding of portfolio management, capacity planning, and demand management practices
• Experience leading PMO, portfolio operations, or technology governance functions
• Executive Presence: Proven ability to communicate with authority and impact, inspiring confidence among executives, stakeholders, and teams
• Leadership & Teaming: Demonstrated success in building strong, collaborative, and diverse teams, with a track record of coaching and mentoring to develop future leaders
• Stakeholder Management: Strong ability to anticipate stakeholder needs, manage expectations, and navigate complex organizational dynamics with diplomacy
• Process & Governance: Expert knowledge of portfolio governance, risk management, and compliance frameworks
• Financial & Business Acumen: Strong financial literacy and the ability to link project execution and outcomes directly to organizational value
• Technical & Domain Knowledge: Solid understanding of agile best practices, financial services, and emerging technologies
• Analytical Skills: Able to spot systemic risks, evaluate trade-offs, and make sound, data-driven decisions
• Proven ability to influence senior leaders and navigate complex organizational trade-offs
• Strong analytical, communication, and executive presentation skills
• Experience leading people and developing talent

The Perks

At FHLBank Chicago, we believe in rewarding our high performing workforce. We offer a highly competitive compensation and bonus package, and access to a comprehensive benefits program designed to meet the needs of our employees. Our retirement program includes a 401(k) and pension plan. Our wellbeing program supports employees at work and in their personal lives: Our PTO plan provides five weeks of vacation for new employees and 11 paid holidays per year; our Lifestyle Spending Account provides an annual stipend for employees to support wellbeing activities; and our central downtown location at the Old Post Office provides easy access to public transportation and breathtaking views from our award-winning rooftop. Visit FHLBCbenefits.com for additional details about our benefits. Step into a brighter future with us

Salary Range:

The above represents the expected salary range for this job requisition.  Ultimately, in determining your pay, we may also consider your experience, and other job-related factors. In addition to the base salary, we offer a comprehensive benefits package which can be found here: https://hrportal.ehr.com/fhlbc