Sr Manager, Application Development (HR/Finance & Delivery Management)

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 Sr. Manager, Application Development is a senior technology leader within IT Software Engineering & Delivery responsible for leading multiple application development teams in the design, development, modernization, delivery, and support of secure, scalable, cloud-enabled enterprise applications that support FHLBank Chicago’s business operations and strategic priorities. This role will provide leadership across two key domains: the Bank’s Human Resources and Finance application portfolio, including Workday and related systems, and the enterprise Agile delivery management practices, roles, tools, and standards used across IT Software Engineering & Delivery. This role requires a highly technical engineering leader who can guide architecture and design decisions, challenge technical assumptions, remove delivery impediments, and ensure teams are building high-quality software using modern engineering practices. The Sr. Manager is expected to be a strong partner to business stakeholders, Product Owners, Enterprise Architecture, Cybersecurity, Infrastructure, Data, Risk, Compliance, and IT leadership to translate business needs into sustainable technology solutions. The ideal candidate has deep experience leading software engineering teams in an Agile Scrum environment, delivering applications on AWS, implementing DevSecOps and CI/CD practices, modernizing legacy platforms, developing technical talent, and building high-performing teams in a regulated financial services environment. The role is accountable not only for delivery execution, but also for engineering excellence, application reliability, security, talent development, and continuous improvement across teams. How you'll make an impact: Provides senior technology leadership across the HR and Finance application portfolio, including Workday, custom applications, SaaS platforms, integrations, workflows, and reporting capabilities, ensuring solutions are secure, scalable, reliable, and aligned to business priorities and outcomes. Be an IT thought leader and drive business value through stronger partnership, talent development, and risk-aware execution, helping HR, Finance, and technology stakeholders translate business needs into sustainable solutions while building high-performing teams and maintaining operational, audit, and compliance readiness. Owns and strengthens Agile delivery across the enterprise by improving delivery predictability, modernizing application development, embedding security and quality earlier in the lifecycle, and using metrics to drive continuous improvement. What you can expect: Technology Leadership & Engineering Excellence Provide technology leadership for the Bank’s Human Resources and Finance application portfolio, including custom-developed applications, SaaS platforms, integrations, reporting capabilities, workflow solutions, and Workday Human Capital Management, Finance, and General Ledger capabilities. Lead the end-to-end software development lifecycle, including solution design, architecture alignment, development, code quality, testing, deployment, operational readiness, and production support. Provide strong technical leadership across application development teams, ensuring solutions are secure, scalable, reliable, maintainable, observable, and aligned with enterprise architecture standards. Partner with business owners and leaders to define, build, maintain, and execute application roadmaps that balance business priorities, platform capabilities, modernization needs, technical debt, operational risk, and delivery capacity. Guide teams in modern engineering practices, including clean architecture, API-first design, microservices where appropriate, reusable components, automated testing, secure coding, code reviews, and CI/CD automation. Serve as a technical escalation point for complex application design, production stability, integration, security, performance, and modernization challenges. Cloud, AWS & DevSecOps Delivery Lead teams responsible for designing, building, deploying, and operating applications in AWS-based cloud environments, with a focus on security, reliability, automation, performance, scalability, and cost-conscious engineering. Drive adoption of cloud-native and modern development patterns, including infrastructure as code, containerized applications, managed cloud services, automated deployment pipelines, and application telemetry. Champion DevSecOps practices that embed security, quality, testing, governance, and compliance throughout the development lifecycle rather than treating them as late-stage activities . ​ Ensure development teams build applications with appropriate monitoring, logging, alerting, traceability, and operational support capabilities to improve reliability and reduce mean time to detect and resolve issues. ​ Agile Scrum Delivery Leadership Own and continuously improve the Bank’s Agile framework, standards, processes, coaching model, and delivery tooling, including Microsoft Azure DevOps, while evaluating opportunities to evolve toward a scaled Agile operating model where appropriate. Lead and mature Agile delivery practices across Scrum and Kanban teams, ensuring strong backlog management, sprint and flow discipline, requirements decomposition, user story quality, dependency management, and measurable delivery outcomes. Provide leadership for enterprise delivery management resources and practices across IT Software Engineering & Delivery, including Scrum Masters and Business Systems Analysts responsible for Agile facilitation, requirements gathering, work decomposition, user story development, backlog refinement, and delivery execution support. Partner closely with Scrum Masters, business stakeholders, and technology leaders to prioritize work, manage dependencies, resolve impediments, and deliver incremental business value. Use Agile delivery metrics, engineering quality measures, and operational data to assess team health, delivery predictability, throughput, cycle time, quality, and continuous improvement opportunities. ​ ​ ​​​​ Business Partnership & Stakeholder Management Serve as a strategic technology partner and thought leader for Human Resources, Finance, and other business stakeholders by building trusted relationships, understanding business processes, communicating tradeoffs, managing expectations, and aligning technology delivery to business value. ​​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. Proactively identify technology opportunities, delivery risks, resource constraints, and modernization needs, and present clear recommendations to leadership. ​ T alent Development & High-Performing Teams Hire, develop, coach, and retain strong Agile and software engineering talent, including managers, scrum masters, business systems analysts, developers, DevOps engineers , quality engineers and application support resources. Build a high-performance engineering culture focused on accountability, craftsmanship, collaboration, continuous learning, inclusion, and strong business partnership. E stablish 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. Ensure SaaS platforms, Workday capabilities, custom applications, integrations, workflows, reporting solutions, and related production changes are appropriately governed, tested, controlled, supported, and aligned with security, compliance, audit, and operational readiness expectations. 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 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, or a related technical discipline; equivalent experience may be considered. 1 5 + years of software engineering and application development experience, including 5+ years managing high-performing engineering teams. Experience leading enterprise application portfolios that include SaaS platforms, custom-developed applications, integrations, reporting, workflow automation, and Workday Human Resources and Finance platforms; experience with Workday quality assurance tools such as Kainos is preferred. Proven success delivering large-scale, business-critical applications using modern software engineering practices, Agile/Scrum methodologies, and AWS cloud technologies. Strong technical expertise in Angular, Java, .NET/.NET Core, APIs, microservices, CI/CD, DevSecOps , automated testing, and cloud-native architectures. Demonstrated experience building, coaching, and developing high-performing engineering teams while driving accountability, continuous improvement, and talent growth. Strong partnership skills with business leaders and cross-functional technology teams to deliver solutions aligned to strategic business objectives . Experience leading application modernization, cloud migration, and digital transformation initiatives within complex, regulated environments. AWS certifications and Agile/project management certifications (e.g., PMP, CSM, PSM, SAFe ) preferred . Experience with GitHub, GitHub Actions, Infrastructure as Code ( IaC ), observability platforms, and modern engineering toolchains preferred. Deep knowledge of modern software engineering, application architecture, cloud-native development, DevSecOps, API integration, and secure coding practices. Strong understanding of AWS services, cloud architecture patterns, automation, scalability, resiliency, observability, and performance optimization. Demonstrated ability to lead Agile/Scrum teams, drive continuous improvement, and deliver predictable, high-quality business outcomes. Exceptional leadership, coaching, and talent development skills with a proven ability to build and sustain high-performing engineering organizations. Strong business acumen and relationship-management skills, with the ability to translate complex business needs into practical technology solutions and influence stakeholders at all levels. Ability to balance innovation, delivery speed, quality, security, and risk management within a highly regulated and complex enterprise environment. Technical Leadership & Software Engineering Excellence Talent Development, Coaching & High-Performing Team Leadership HR, Finance, SaaS, Workday & Integration Platform Leadership Agile, Scrum, Kanban & Scaled Delivery Practices Azure DevOps, Delivery Metrics & Agile Tooling Governance Business Relationship Management, Stakeholder Engagement & Tradeoff Management Risk Management, Operational Readiness & Regulatory Compliance ​ 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: $151,025.00 - $265,525.00 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: