Director, Strategic Portfolio Management

FHLBank Chicago•Chicago, IL

2d•$181,125 - $318,675•Hybrid

About The Position

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.

Requirements

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 Technology, 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

Responsibilities

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
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
Lead enterprise portfolio planning activities, 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
Oversee portfolio health reporting, executive dashboards, KPIs, and strategic initiative metrics
Deliver 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 transparency and reporting capabilities
Lead and develop a portfolio management team including: Intake & Prioritization Lead, Resource & Capacity Planner, Portfolio Data Analytics Lead, Program & Project Managers
Foster a culture of collaboration, accountability, continuous improvement, and strategic partnership
Build strong relationships across business, technology, finance, and executive leadership teams