Manager, Strategic Planning

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 role is accountable for leading, managing, and continuously improving the Bank’s strategic planning process and delivering the Bank’s annual Strategic Plan. This role partners closely with stakeholders across the Bank to develop a comprehensive strategy aligned with the Bank’s mission, vision, goals, and long-term priorities. The position is responsible for coordinating the annual strategic planning calendar, developing materials for senior leadership, the Board, regulators, employees, and other stakeholders, and creating mechanisms to monitor progress against the plan. The role requires a high degree of independent thinking, resourcefulness, organization, and judgment, including the ability to lead strategic initiatives, manage ad hoc executive requests, identify risks or gaps, and drive work forward with limited direction. The ideal candidate will possess strong analytical, communication, and stakeholder management skills, with the ability to clearly convey complex concepts to audiences at all levels of seniority across the Bank. How you'll make an impact Leads and continuously improves the Bank’s strategic planning process, ensuring alignment between strategy, execution, and measurable outcomes. Provides enterprise-wide leadership, accountability, and governance for development and delivery of the Strategic Plan. Enables informed executive and Board decision-making through strategic analysis, performance reporting, and executive communications. Strengthens cross-functional alignment and drives execution of strategic priorities across the organization. Enhances monitoring of strategic goals, incentive objectives, and key performance metrics to improve accountability and results. Coordinates critical Board, regulatory, compliance, and FHFA-related strategic planning activities. Identifies risks, opportunities, and emerging issues to support proactive management and long-term success. Improves employee understanding and engagement by connecting day-to-day work to the Bank’s strategic objectives. What you can expect Lead and manage the Bank’s annual strategic planning process, including maintaining and refining the strategic planning calendar, coordinating stakeholder expectations, and ensuring key deadlines and deliverables are met. Develop comprehensive strategic plans aligned with the Bank’s mission, vision, strategic priorities, goals, and objectives. Collaborate with Executive Team members, senior leaders, and cross-functional stakeholders to gather input, challenge assumptions, identify risks and opportunities, and inform the strategic planning process. Independently lead and support strategic initiatives, special projects, research efforts, and ad hoc requests from executives, Internal Audit, regulators, and other areas of the Bank. Develop, refine, and deliver presentations and materials tailored to a range of audiences, including the Executive Team, Board of Directors, regulators, employees, and other stakeholders. Develop monitoring tools, reporting, and performance updates to track progress against the Strategic Plan, key strategic priorities, metrics, and incentive goals; recommend adjustments as needed. Work closely with the Income Simulation team and other subject matter experts to understand the Strategic Plan’s impact on the Bank’s financial projections, key assumptions, and potential downside scenarios. Support the development, tracking, and reporting of short-term and long-term incentive goals that align with the Bank’s strategic priorities and Board-approved objectives. Develop a deep understanding of the Bank’s operating model, cost structure, revenue drivers, financial projections, and strategic priorities to extract actionable insights and support informed decision-making. Coordinate legal, regulatory, compliance, and control-related activities associated with the Strategic Plan, including supporting required reviews, certifications, Board approvals, and FHFA submission requirements. Represent the Bank in system-wide strategic planning forums and participate in Bank projects to help ensure alignment with the Bank’s strategy and long-term vision. Manage or facilitate updates to policies owned by the CFO or Manager, Strategic Planning, including coordinating stakeholder review, approvals, version control, and submission to the Policy Library. Prepare and deliver employee-facing strategic planning materials, including department roadshow presentations, SharePoint updates, and other communications that help employees understand how their work connects to the Bank’s strategy. Encourage teamwork, professionalism, accountability, and strong stakeholder engagement across the team and throughout the Bank. What you'll bring Bachelor’s degree in business, Finance, Economics, Strategy, Analytics, or a related field required. Master’s degree preferred. 8–10 years of overall work experience preferred, including experience in roles requiring strategic thinking, analytical problem-solving, stakeholder collaboration, executive-level communication, and independent ownership of complex deliverables. Experience supporting strategic planning, financial planning, performance reporting, executive communications, business analysis, or enterprise-wide initiatives preferred. Strong leadership, management, stakeholder engagement, and coaching skills. High degree of independent thinking, sound judgment, resourcefulness, organization, professionalism, and logical reasoning. Ability to independently manage complex initiatives, competing priorities, interruptions, and multiple workstreams with limited direction. Strong analytical and problem-solving skills, with the ability to interpret financial, operational, and strategic data to inform decision-making. Excellent written, verbal, and presentation skills, with the ability to communicate complex ideas clearly and persuasively to employees, senior leaders, executives, the Board, regulators, and other stakeholders. Demonstrated ability to collaborate effectively with cross-functional teams, influence decision-making, and manage stakeholders with competing viewpoints. Strategic mindset with the ability to think critically, challenge assumptions, anticipate future trends, and identify gaps, inconsistencies, risks, and opportunities. Proven ability to use business intelligence, reporting, presentation, and analytical tools to develop insights, monitor performance, and support strategic decision-making. Ability to drive accountability while maintaining a positive, collaborative, and professional approach to stakeholder management. 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 for additional details about our benefits. Step into a brighter future with us. Salary Range: $125,825.00 - $221,275.00 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: