Manager Sales Enablement

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

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The Manager, Sales Enablement builds and leads the Bank’s dedicated Sales Enablement function, equipping the sales organization, the broader Bank, and participating financial institutions (PFIs) with the skills, education and tools to execute against the Bank’s commercial strategy. This role owns sales process and opportunity discipline; translation and simplification of complex product, policy, and market developments into practical guidance; sales tools, content, and sales strategies; training and coaching; and MORE (Member Outreach) administration.

The Manager designs the playbooks, curricula, content standards, and Salesforce workflows that make member engagement consistent, risk-aware, and effective. This is a builder’s role: Sales Enablement does not exist as a dedicated function at the Bank today, and this leader will stand it up as a 2026 pillar.

This position sits within the Member Financial Strategies group, reports to the group’s senior leader, and leads a team that includes a Sales Enablement Analyst and the MORE and organizational-training anchor. It engages cross-functionally with Sales, Solutions, First Line of Defense, MPF Sales, Product Development, Marketing and Communications, and the Customer Experience group.

How you'll make an impact

• Help define and build the Sale Enablement function. Design and implement the enablement engine, shaping how the Bank engages members and drives commercial growth for years to come.

• Turn complexity into action. Help sales teams and member institutions navigate complex products, policies, and market developments through practical tools, training, and guidance.

• Equip the sales organization sell with confidence. Design the playbooks, training programs, and processes that enable more consistent, effective, and risk-aware member engagement across the Bank.

What you can expect

Sales Process & Opportunity Discipline

• Standardize how opportunities are initiated, developed, coordinated, and advanced across the sales organization

• Design and maintain Salesforce workflows, stages, and discipline that support a consistent, well-managed pipeline

• Define and reinforce the cadence, hand-offs, and accountabilities that keep member engagements moving

Translation & Simplification

• Convert complex product, policy, and market developments into practical, sales-ready guidance

• Partner with Solutions and First Line of Defense to ensure messaging is accurate, suitable, and on-strategy

• Maintain plain-language reference materials that help the sales force engage members with confidence

Sales Tools, Content & Pitchbooks

• Curate and standardize sales materials, templates, and pitchbooks

• Establish and maintain a single source of truth for approved sales content, with clear version control

• Ensure content is consistent, on-brand, compliant, and easy for the sales force to deploy

Training & Coaching

• Build and deliver sales training on risk-aware execution, and broader organizational training on business changes

• Design onboarding programs and progressive development curricula using sound adult-learning principles

• Partner with the MORE and organizational-training anchor to plan and deliver training across the organization

MORE Administration (PFI-facing)

• Oversee MORE engagements that ensure PFIs underwrite to FHLB standards

• Coordinate PFI-facing engagements that support the production pipeline and reinforce underwriting-standard alignment

Team Leadership & Talent Development

• Directly manage and develop a team

• Set priorities, allocate workloads, and maintain high standards across enablement deliverables

• Review and quality-control enablement content, curricula, and reporting prior to release

What you'll bring

• Bachelor’s degree in Business, Marketing, Finance, Communications, or a related field. Advanced degree (MBA) or relevant certification is a plus.

• 7+ years of professional experience in sales enablement, sales operations, product marketing, training and learning & development, or commercial strategy—preferably in financial services—including 1–3 years of people leadership experience.

• Demonstrated experience building enablement programs, playbooks, curricula, or standardized content from the ground up.

• Hands-on experience designing and maintaining Salesforce (or comparable CRM) workflows and reporting.

• Proven ability to translate complex financial products and policy into clear, sales-ready guidance.

• Sales process design and CRM/Salesforce workflow discipline.

• Skill at translating complex product, policy, and market developments into clear, practical guidance.

• Curriculum design and adult-learning delivery, with strong facilitation and coaching ability.

• Content and pitchbook standardization, with an eye for consistency, brand, and compliance.

• Exceptional written and verbal communication skills, with executive presence and the ability to influence

• Strong cross-functional partnership skills

• Proven ability to set direction, manage workloads, and develop talent within a team.

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.