Jobs at Federal Home Loan Bank of Chicago (Now Hiring) — 9 open

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 technology leadership for the Bank’s member engagement, Salesforce, and governance/risk/compliance application portfolios, including a mix of custom-developed applications, SaaS platforms, workflow solutions, reporting capabilities, integrations, and Salesforce ecosystem capabilities that support business engagement, operational effectiveness, risk management, and regulatory alignment.

How you'll make an impact:

• Provides senior technology leadership across the Bank’s member engagement, Salesforce, CRM, and GRC application portfolio, including custom applications, SaaS platforms, Salesforce ecosystem capabilities, integrations, workflows, and reporting solutions, ensuring platforms are secure, scalable, reliable, supportable, and aligned to business priorities and outcomes.

• Serves as an IT thought leader and drives business value through strong partnership, platform maturity, talent development, and risk-aware execution, helping member engagement, risk, governance, compliance, and technology stakeholders translate business needs into sustainable solutions while building high-performing teams and maintaining operational, audit, and regulatory readiness.

• Strengthens Agile delivery, modern engineering practices, and Salesforce platform governance by improving IT delivery predictability, managing business and technology tradeoffs, 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 across the Bank’s member engagement and Salesforce application portfolio, ensuring custom applications, SaaS platforms, integrations, reporting capabilities, workflow solutions, and Salesforce ecosystem components are reliable, secure, scalable, supportable, and aligned with business objectives.

• 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.

• 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.

• Partner with architects, engineering leads, business owners, and stakeholders to evaluate technical and business tradeoffs, reduce technical debt, strengthen platform maturity, and ensure application platforms remain fit for purpose as business needs evolve.

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

• Lead application development teams operating in Agile/Scrum delivery models, ensuring teams maintain strong sprint discipline, predictable delivery planning, effective backlog refinement, and measurable delivery outcomes.

• Partner with Product Owners and business leaders to define, maintain, and execute application roadmaps that balance strategic business value, stakeholder priorities, Salesforce platform health, regulatory needs, technical debt, and team capacity.

• 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

• Build strong, trusted partnerships with business leaders and stakeholders across member engagement/CRM, risk, governance, and compliance functions by understanding business processes, priorities, risks, value drivers, stakeholder expectations, and desired outcomes.

• Translate business needs into clear technology roadmaps, system capabilities, delivery plans, and technical solutions that support FHLBC’s strategic objectives.

• Lead effective stakeholder management and tradeoff conversations with business partners, helping align scope, timing, cost, risk, quality, Salesforce platform capability, and business value when prioritizing roadmaps, enhancements, operational needs, and delivery commitments.

• 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.

Talent Development & High-Performing Teams

• Hire, develop, coach, and retain strong software engineering talent, including managers, technical leads, developers, cloud engineers, test engineers and application support resources.

• 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

• 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 and support a blended application portfolio that includes custom-developed solutions, SaaS platforms, Salesforce capabilities, vendor-supported applications, integrations, workflow tools, and reporting solutions, ensuring clear ownership, lifecycle planning, vendor accountability, and operational support.

• 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.

• 15+ years of software engineering and application development experience, including 5+ years managing high-performing engineering teams.

• 8+ years hands-on leadership experience with the Salesforce ecosystem, preferably including Sales Cloud, Marketing Cloud, Service Cloud, integrations, platform governance, release management, and cross-functional delivery in an enterprise environment.

• Experience leading technology delivery and support for Salesforce, member/customer engagement, governance, risk, compliance, workflow, reporting, and SaaS-based application portfolios.

• 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.

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:

$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: https://hrportal.ehr.com/fhlbc