Federal Home Loan Bank of Chicago · 1 month ago
Senior Sales Enablement Trainer
Chicago
Full-time
Onsite
Mid, Senior Level
$108K/yr - $181K/yr
4+ years expThe Federal Home Loan Bank of Chicago is a strategic partner for financial institutions, focused on community investment. The Senior Sales Enablement Trainer will design and deliver training programs that help member institutions and internal stakeholders understand and effectively use FHLBank products and services.
Banking
Responsibilities
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 training effectiveness through participation data and feedback, use insights to improve programs, and partner with Risk, Legal, and Compliance to ensure all external materials meet required standards
Qualification
Required
Bachelor's degree in Business, Finance, Education, communications, or a related field
4-7 years of experience in sales enablement, training/learning & development, or client education—ideally within financial services or B2B environments
Familiarity with banking, capital markets, liquidity, mortgage origination, or secondary market processes, and a strong willingness to deepen product expertise
Ability to design adult learning experiences and instructional materials that simplify complex topics for diverse audiences
Exceptional presentation and facilitation skills, with confidence engaging both technical and executive-level participants
Strong collaboration skills and experience working with Sales and Product teams to align training with business goals
Comfort using virtual training platforms and learning tools; experience with learning management or content management systems is a plus
A continuous improvement mindset, with the ability to incorporate feedback, data, and emerging best practices into program design and delivery
Benefits
Retirement program (401k and Pension)
Medical, dental and vision insurance
Lifestyle Spending Account
Competitive PTO plan
11 paid holidays per year
Company
Federal Home Loan Bank of Chicago
Our Mission: To partner with our members in Illinois and Wisconsin to provide them competitively priced funding, a reasonable return on their investment in the Bank, and support for their community investment activities.
201-500 employees
Funding
Current Stage
Growth StageLeadership Team
Eric Geiger
Chief Technology Officer
Mike Zeifert, CFA
SVP, Chief Credit Officer
Company data provided by crunchbase