Manager Sales Enablement

Federal Home Loan Bank of Chicago•Chicago, IL

8d•Hybrid

About The Position

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.

Requirements

Bachelor’s degree in Business, Marketing, Finance, Communications, or a related field.
7+ years of professional experience in sales enablement, sales operations, product marketing, training and learning & development, or commercial strategy—preferably in financial services
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.

Nice To Haves

Advanced degree (MBA) or relevant certification is a plus.

Responsibilities

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.
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
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
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
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
Oversee MORE engagements that ensure PFIs underwrite to FHLB standards
Coordinate PFI-facing engagements that support the production pipeline and reinforce underwriting-standard alignment
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