Manager, Application Development

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 ​ What you'll do The Manager, Application Development is a technology leader within IT Software Engineering & Delivery responsible for leading Agile Delivery capabilities across the department, including Scrum Masters and Business Systems Analysts supporting 10+ delivery teams and 100+ applications. This role is accountable for strengthening Agile execution, business analysis practices, delivery transparency, stakeholder alignment, and predictable delivery outcomes across a broad portfolio of business-critical technology solutions. This role requires a strong IT leader with software development delivery experience who can partner effectively with business stakeholders, Product Owners, application development teams, Enterprise Architecture, Cybersecurity, Infrastructure, Risk, Compliance, and IT leadership. The Manager is expected to help teams translate business needs into well-defined priorities, facilitate trade-off conversations, remove delivery impediments, and ensure Agile practices are consistently applied to support measurable business and technology outcomes. The ideal candidate has deep experience leading Agile delivery teams, Scrum Masters, and Business Systems Analysts in a complex software development environment. The role is accountable for owning and maturing the Bank’s Agile framework, establishing related standards and processes, driving effective use of Microsoft Azure DevOps, strengthening Agile metrics and delivery reporting, and evaluating future opportunities to evolve toward a scaled Agile operating model where appropriate How you'll make an impact: Owns and matures the Bank’s Agile delivery framework by leading Scrum Masters and Business Systems Analysts across Software Engineering & Delivery, standardizing Scrum/Kanban practices, strengthening backlog and requirements discipline, and coaching teams to improve delivery consistency, transparency, predictability, and continuous improvement. Drives Azure DevOps standards, metrics, and delivery transparency by defining consistent practices for boards, backlogs, work item hierarchy, dashboards, queries, reporting, delivery metrics, and data quality, enabling stronger visibility into team health, dependencies, risks, delivery predictability, and continuous improvement opportunities. Strengthens business partnerships and delivery outcomes while advancing the Bank toward scaled Agile maturity by partnering with IT and business leaders to improve cross-team planning, dependency management, stakeholder alignment, trade-off decision-making, and Agile operating model readiness across 10+ delivery teams and 100+ applications. What you can expect: Technology Leadership & Agile Excellence Lead Agile Delivery capabilities across multiple software delivery teams, ensuring Scrum Masters and Business Systems Analysts are effectively supporting planning, prioritization, requirements readiness, delivery execution, and continuous improvement. Provide strong IT delivery leadership across application teams by understanding software development practices, technology dependencies, delivery risks, quality considerations, and business priorities. Own and mature the Bank’s Agile delivery framework, including standards, ceremonies, role expectations, backlog practices, estimation guidance, delivery metrics, team working agreements, and continuous improvement routines. Coach teams on effective Scrum and Kanban practices to improve transparency, flow, prioritization, dependency management, impediment resolution, and predictable delivery outcomes. Partner with application development leaders, Product Owners, architects, QA, and business stakeholders to ensure Agile practices support high-quality software delivery, operational readiness, risk management, and business value realization. Azure DevOps Ownership, Metrics & Delivery Transparency Own Microsoft Azure DevOps as the department’s primary Agile planning and delivery management platform, ensuring it effectively supports backlog management, sprint planning, Kanban flow, dependency tracking, delivery reporting, and leadership visibility. Define, govern, and continuously improve Azure DevOps usage standards, including work item hierarchy, board configuration, tagging, dashboards, queries, metrics, reporting practices, and data quality expectations. Establish and monitor Agile delivery metrics, including team health, throughput, cycle time, sprint predictability, backlog readiness, aging work items, defect trends, dependency risks, and continuous improvement opportunities. Use delivery data and Agile metrics to identify trends, highlight risks, improve planning, support capacity discussions, and enable fact-based conversations with IT leadership and business partners. Drive consistent delivery transparency across teams to support stakeholder communication, leadership decision-making, prioritization, risk management, and continuous improvement. Scrum Master & Business Systems Analysis Leadership Directly lead, coach, and develop Scrum Masters and Business Systems Analysts across the department, ensuring both roles provide strong delivery leadership, stakeholder engagement, business analysis discipline, and team facilitation. Set clear role expectations, standards, and operating practices for Scrum Masters and Business Systems Analysts to ensure consistent execution across delivery teams. Coach Scrum Masters on facilitation, impediment removal, team health, sprint planning, retrospectives, Kanban flow, continuous improvement, and effective Agile practices. Coach Business Systems Analysts on requirements elicitation, process analysis, user story development, acceptance criteria, backlog readiness, stakeholder alignment, and solution readiness. Strengthen collaboration between Product Owners, Scrum Masters, Business Systems Analysts, development teams, QA, architecture, and business partners to improve end-to-end software delivery outcomes. ​​​​​​ Business Partnership & Stakeholder Management Build strong, trusted partnerships with business leaders and stakeholders by understanding business processes, priorities, risks, and desired outcomes. Translate business needs into clear technology roadmaps, system capabilities, delivery plans, and technical solutions that support FHLBC’s strategic objectives. Communicate effectively with technical and non-technical audiences, including senior leadership, business partners, risk/compliance stakeholders, vendors, and delivery teams. Build strong, trusted relationships with business partners by helping teams understand business priorities, clarify desired outcomes, and translate needs into actionable delivery plans. Facilitate effective trade-off conversations with business stakeholders, including scope, timing, sequencing, capacity, risk, quality, dependencies, and business value. Ensure business partners have clear visibility into delivery priorities, status, risks, dependencies, decision points, and delivery impacts. Proactively identify technology opportunities, delivery risks, resource constraints, and modernization needs, and present clear recommendations to leadership. ​ Talent Development & High-Performing Teams Hire, develop, coach, and retain strong Agile delivery talent, including Scrum Masters and Business Systems Analysts, while building a high-performing culture focused on accountability, collaboration, Agile discipline, business partnership, software delivery excellence, and continuous improvement. Build a high-performance engineering culture focused on accountability, craftsmanship, collaboration, continuous learning, inclusion, and strong business partnership. Establish clear performance expectations, provide timely feedback, support career development, and create growth paths for emerging technical and leadership talent. Develop succession plans, strengthen team capability, and ensure the organization has the skills required to support modern cloud-based software development. Foster psychological safety, collaboration, and ownership while holding teams accountable for delivery commitments, software quality, security, and operational outcomes. Risk, Security, Compliance & Operational Readiness Ensure applications and engineering practices meet applicable security, compliance, audit, and regulatory expectations within a financial services environment. Partner with Cybersecurity, Risk, Compliance, Audit, and Infrastructure teams to ensure appropriate controls are embedded into application design, development, testing, release, and support processes. Promote secure coding, threat-aware design, vulnerability remediation, automated testing, segregation of duties, change control, and evidence-based audit readiness. Ensure production changes are well-controlled, appropriately tested, observable, and aligned with enterprise risk management expectations. Strategy, Planning & Financial Management Partner with IT leadership to mature the Bank’s Agile delivery model, including assessing readiness for scaled Agile practices, improving cross-team planning, strengthening dependency management, standardizing Agile practices, and aligning delivery execution to strategic priorities. Contribute to application portfolio strategy, technology roadmaps, annual planning, budgeting, staffing models, and resource allocation. Support modernization initiatives involving digital transformation, application rationalization, API integration, platform resiliency, data integration, and legacy system transformation. Manage vendor and third-party delivery relationships as needed, ensuring external partners meet quality, delivery, security, and architectural expectations. Track delivery performance, team capacity, financial impacts, operational health, and modernization outcomes to support leadership decision-making. What you’ll bring: Bachelor's or Master's degree in Computer Science, Engineering, Information Systems, Business Administration, or a related discipline; equivalent experience may be considered. 10+ years of technology delivery, software development delivery, business analysis, Agile delivery, application delivery, or related IT experience, including 3+ years managing teams or delivery functions. Proven success leading Agile delivery practices across multiple software delivery teams using Scrum, Kanban, Azure DevOps, backlog management, stakeholder engagement, delivery metrics, and continuous improvement methods. Demonstrated experience leading, coaching, or developing Scrum Masters, Business Systems Analysts, Product Owners, delivery teams, or related Agile delivery roles. Strong understanding of the software development lifecycle, including solution delivery, requirements definition, application development, testing, release readiness, production support, risk management, and operational considerations. Experience establishing Agile standards, improving delivery predictability, strengthening business analysis practices, and using data-driven insights to improve team performance and delivery outcomes. Strong partnership skills with business leaders and cross-functional technology teams to facilitate prioritization, manage trade-offs, resolve impediments, and deliver solutions aligned to strategic business objectives. Experience with scaled Agile practices, enterprise Agile transformation, Agile operating model maturity, or multi-team delivery coordination preferred. Agile certifications such as CSM, PSM, PMI-ACP, SAFe, PMP or equivalent practical experience preferred. Experience with Microsoft Azure DevOps, delivery dashboards, Agile metrics, workflow configuration, and enterprise reporting practices. Deep knowledge of Agile delivery practices, including Scrum, Kanban, backlog management, sprint planning, flow management, dependency tracking, delivery metrics, and continuous improvement. Strong understanding of business analysis practices, including requirements elicitation, process analysis, user story development, acceptance criteria, stakeholder alignment, traceability, and solution readiness. Demonstrated ability to lead Scrum Masters and Business Systems Analysts across multiple software delivery teams while setting consistent standards, expectations, and coaching practices. Strong understanding of the software development lifecycle, with the ability to partner effectively with application development, QA, architecture, infrastructure, cybersecurity, risk, compliance, and business teams. Strong Azure DevOps knowledge, including boards, backlogs, dashboards, queries, work item management, metrics, reporting, delivery transparency, and standards governance. Strong business acumen and stakeholder management skills, with the ability to facilitate trade-off conversations and align technology delivery with business priorities. Ability to mature an enterprise Agile operating model while balancing delivery speed, quality, transparency, risk management, organizational readiness, and business value. Agile Delivery, Scrum/Kanban, Scrum Master & Business Systems Analysis Leadership Technical Leadership & Software Engineering Excellence Talent Development, Coaching & High-Performing Team Leadership Software Delivery Lifecycle & IT Delivery Leadership Azure DevOps Ownership, Standards & Reporting Delivery Metrics, Team Health & Continuous Improvement Business Relationship Management, Stakeholder Management, Business Partnership & Trade-Off Facilitation Scaled Agile Readiness & Agile Operating Model Maturity Risk Management, Secure Software Development & Regulatory Compliance 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: