Senior Sales Enablement Trainer

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

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.

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.

The Senior Sales Enablement Trainer is a strategic partner to our Sales and Member Strategy teams, responsible for turning complex FHLBank products and programs into clear, practical learning for our member institutions and for internal stakeholders including the sales team. You will design and deliver training that helps members and sales better understand, position, and use our products and services—such as Lending Products (advances), Letters of Credit, Secondary Mortgage Market Products (MPF) community investment offerings (Discounted lending and Grants).

Through a mix of live, virtual, and on‑demand education, you’ll build a scalable member training program that deepens engagement and supports the Bank’s growth objectives.

• You will strengthen member relationships by equipping lenders, treasurers, and executives with the knowledge and confidence to use FHLBank Chicago products effectively.
• Your training programs will support key business priorities, including product adoption, new member onboarding, MPF usage, and deeper market share with existing members.
• By building a cohesive member education strategy and partnering closely with Sales and Product teams, you’ll help create a more consistent, high‑quality experience for members across Illinois and Wisconsin.

• Develop and maintain a training roadmap and training calendar aligned to Bank, Sales, and product priorities.
• Design and deliver engaging training experiences (webinars, workshops, conferences, office hours) that translate complex FHLBank concepts into clear, member‑friendly stories and real‑world use cases.
• Serve as a Subject Matter Expert (SME) for internal and external parties on Bank, agency, and investor underwriting guidelines and policies, while identifying and reporting secondary market eligibility requirements and providing feedback to member institutions as part of the mortgage review process.
• Build and continuously refine specialized training on the end‑to‑end mortgage process—including origination, underwriting, delivery via technology, servicing options, and collateralization (haircuts/discounts)—using checklists, flowcharts, and practical job aids.
• Collaborate with Sales, Product, Collateral, Credit, Marketing, and Community Investment teams to ensure content is accurate, timely, and aligned with campaigns, product launches, product materials and member outreach.
• Measure…