Sr. Managing Director, Project Management Office

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 Senior Managing Director will report directly into the Chief Information Officer (CIO) and will lead the PMO, (Portfolio/Program/Project) Management Office. This role will be responsible for:

• transforming and maturing the existing PMO
• evolving the PMO’s relationships with business stakeholders and foster seamless execution in alignment with Agile best practices
• lead the PMO team members and create a standard for high performance
• providing oversight of the Bank’s technology project portfolio
• intersecting with C-level and other executive audiences

This role requires a visionary leader who can drive cultural and structural change, not just manage existing processes. This role will be an extension of the technology senior leadership team and will serve as a bridge between the Bank's Business and IT teams. This role involves leading a team of project managers who function as trusted advisors to executives and business leaders, providing Portfolio and Program advisory up to the Board level. This position is highly visible.

This person should:

• be comfortable establishing fit-for-purpose methodology alignment, with deep understanding Agile best practices
• bring a hybrid of industry and consulting experience 
• demonstrate a history of leading organizations through significant change, rather than maintaining the status quo
• demonstrate strong executive presence, interpersonal communication, and influence
• bring experience in building, inspiring, motivating, and developing high-performing teams through periods of change and ambiguity

How you’ll make an impact:

• Drive transformation and alignment - redefine and mature the PMO to operate as a strategic partner to the business, ensuring technology investments directly enable the Bank's strategic objectives
• Elevate execution and governance - implement processes, tools and governance that enhance visibility, accountability, and delivery across the enterprise portfolio.
• Inspire high performance - build and lead a world-class PMO team that exemplifies collaboration, agility, and excellence in execution through periods of change and growth

What you can expect:

• Lead Strategy & Change: Act as a transformative leader and a change agent to redefine and lead the PMO, executing its strategic roadmap to ensure the portfolio aligns with Bank objectives, capacity, and measurable business outcomes. Assess the current state of the PMO and design a roadmap for maturity, scalability, and long-term sustainability.
• Drive Process Improvement: Initiate the adoption of new tools and processes to enhance efficiency, transparency, and agility across all projects.
• Engage Stakeholders: Build executive confidence by framing complex decisions with actionable recommendations for senior leaders and the Board.
• Ensure Executive Communication: Define communication standards and ensure the delivery of clear, credible, and outcome-focused board-level reports and executive briefings, covering status, risks, and leadership decisions.
• Demonstrate Strong People Leadership: Build a high-performing team and foster a culture of collaboration and continuous improvement
• Establish Governance and Oversight: Define, refine, and enforce comprehensive program and project management frameworks, risk management practices, and portfolio governance. Partner with Finance and senior leaders to track project investments, ensure cost-effective delivery, and articulate business value.
• Oversee Project Intake: Support the entire intake process, collaborating on business case development, value realization, resource allocation, and cost-benefit analysis.

What you’ll bring:

• Bachelor’s degree in Business Administration, Finance, Information Technology, or related field required.
• Master’s degree (MBA or equivalent) preferred.
• Minimum 15 years of progressive project and portfolio management experience.
• At least 5 years in leadership roles, managing large teams and senior stakeholders.
• Experience in both top-tier consulting environments and leadership roles within industry organizations is highly desirable
• Proven track record leading complex, cross-functional projects within financial services, banking, or highly regulated industries.
• Experience using portfolio management tools (e.g., Clarity PPM, Planview, Smartsheet, or similar).
• Executive Presence: Proven ability to communicate with authority and impact, inspiring confidence among executives, stakeholders, and teams. Ability to influence and gain buy-in from C-level executives for major transformation initiatives.
• 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.
• Project Delivery Expertise: Deep experience leading large-scale, cross-functional initiatives with proven delivery of strategic outcomes.
• 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.

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