Sr. Managing Director, Project Management Office

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. 

• Collaborative, 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

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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 sustainabil