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Director Learning Strategist Jobs in Chicago, IL

Mem Global

JLC Learning Manager

Chicago, IL

You'll work closely with and in direct support of the Director, Learning, who sets the vision and strategy for how every learner and educator experiences JLC. Your job is to bring that vision to life ...

Northwestern University

Learning Engineer

Evanston, IL · On-site

$72.34K - $86K/yr

... Director of Learning Development and Academic Technology in the School of Communication. The ... Teach faculty new delivery strategies and pedagogy options. Monitor and maintain the accessibility ...

CDW

Sr Learning and Development Specialist

Chicago, IL · On-site

This position partners closely with the Director, Learning Strategy and Design, the broader Talent Team, HR Business Partners, and business stakeholders to build scalable, effective, and consistent ...

CDW

Sr Learning and Development Specialist

Chicago, IL · On-site

This position partners closely with the Director, Learning Strategy and Design, the broader Talent Team, HR Business Partners, and business stakeholders to build scalable, effective, and consistent ...

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$100.4K

$146.8K

$200.4K

How much do director learning strategist jobs pay per year?

As of May 28, 2026, the average yearly pay for director learning strategist in Chicago, IL is $146,757.00, according to ZipRecruiter salary data. Most workers in this role earn between $110,200.00 and $181,300.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Director Learning Strategist, and why are they important?

To thrive as a Director Learning Strategist, you need expertise in instructional design, adult learning theory, and strategic planning, usually supported by an advanced degree in education, instructional design, or a related field. Familiarity with learning management systems (LMS), e-learning development tools, and data analytics software is essential. Strong leadership, communication, and change management skills help drive organizational learning initiatives and foster collaboration. These competencies are crucial to designing impactful learning programs that align with business goals and promote continuous professional development.

What are some common challenges faced by a Director Learning Strategist when aligning training initiatives with organizational goals?

A Director Learning Strategist often faces the challenge of ensuring that learning programs are closely aligned with evolving business objectives and measurable outcomes. Balancing diverse stakeholder expectations, managing budget constraints, and integrating new technologies can also be demanding. To overcome these challenges, it is crucial to maintain ongoing communication with leadership, regularly assess learning needs, and adapt strategies to address shifting priorities. Collaborating with cross-functional teams and demonstrating the impact of learning initiatives on business performance are essential aspects of the role.

What does a Director Learning Strategist do?

A Director Learning Strategist is responsible for developing and overseeing the educational strategy within an organization. They design and implement learning programs that align with business goals, ensuring that employees have the skills and knowledge needed to succeed. This role often involves collaborating with other leaders, evaluating the effectiveness of training initiatives, and staying current with trends in adult learning and technology. Ultimately, their work helps drive organizational growth and employee development.
What are the most commonly searched types of Learning Strategist jobs in Chicago, IL? The most popular types of Learning Strategist jobs in Chicago, IL are:
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Director Learning Strategist jobs near you
Director, Learning & Development, GOS

Director, Learning & Development, GOS

Cushman & Wakefield

Chicago, IL • On-site

Full-time

Medical, Dental, Vision, Life, Retirement

Posted 18 days ago

Cushman & Wakefield rating

7.6

Company rating: 7.6 out of 10

Based on 149 frontline employees who took The Breakroom Quiz

69th of 152 rated real estate companies

Job description

Job Title
Director, Learning & Development, GOS
Job Description Summary
Role Overview
Cushman & Wakefield is seeking a Director, Learning & Development, to lead the design and execution of a modern, global learning strategy for Global Occupier Services (GOS). This role will be instrumental in building the learning strategy for the future of work, with a heavy emphasis on AI enablement, digital upskilling, leadership capability, and business critical skills that accelerate performance, productivity, and growth.
As a senior leader within the People organization, this role will define how learning drives business outcomes, moving beyond traditional training toward capability building, behavior change, and measurable impact. The Director will partner closely with GOS leadership, HR, Technology & Data Solutions, and Operations to ensure learning is practical, scalable, and embedded in how the business operates.
This is a strategy first, execution-oriented role, responsible for setting vision, building frameworks, and ensuring delivery that equips leaders and teams to thrive in an increasingly AI-enabled, data driven environment.
Job Description
Key Responsibilities
Learning Strategy & AI Enablement
  • Define and lead the GOS Learning & Development strategy, aligned to business priorities, growth objectives, and the future capabilities required across the organization.

  • Design and scale a comprehensive AI upskilling strategy, enabling leaders and employees to effectively adopt, understand, and apply AI and digital tools in their roles.

  • Establish role-based learning paths and capability frameworks across leadership, professional, operational, and technical roles, with clear proficiency expectations.

  • Partner with Technology, Data, and Product leaders to ensure learning supports technology adoption, workflow integration, and measurable productivity gains.

Leadership & Capability Development
  • Architect and deliver global leadership development programs that build inclusive, resilient, and future ready leaders aligned with Cushman & Wakefield's values and GOS strategy.

  • Translate complex business, leadership, and AI concepts into practical, engaging learning experiences that drive real behavior change.

  • Embed learning into moments that matter, onboarding, role transitions, organizational change, and critical business initiatives.

Design, Delivery & Innovation
  • Oversee the design and development of high impact learning solutions across modalities, including:

  • Instructor led and virtual programs

  • Digital and AI enabled learning experiences

  • Role based curricula and learning journeys

  • Job aids, playbooks, and performance support tools

  • Champion innovative learning approaches, staying current on emerging learning technologies, AI trends, and best practices.

  • Ensure learning solutions are scalable, globally relevant, and tailored to the realities of a complex, client-facing business.

Governance, Measurement & Impact
  • Establish strong governance, standards, and a single source of truth for GOS learning content.

  • Define and track learning effectiveness, adoption, and capability outcomes, using data to continuously improve and retire outdated content.

  • Provide executive ready insights on learning impact, risks, and opportunities, clearly linking learning investments to business results.

Stakeholder & Vendor Management
  • Serve as a trusted advisor to senior GOS leaders, HR partners, and functional stakeholders.

  • Lead and manage external vendors and partners to ensure quality, alignment, and outcomes.

  • Build strong collaboration across regions, functions, and time zones, bringing a global mindset to all initiatives.

Qualifications & Experience
Required
  • Bachelor's degree in education, Instructional Design, Organizational Development, HR, or related field (or equivalent experience).

  • 8-10+ years of progressive experience in Learning & Development, with demonstrated success building enterprise level learning strategies.

  • Proven experience designing and scaling leadership development and digital/technology enabled learning programs.

  • Strong understanding of AI, digital transformation, and technology adoption as it relates to workforce capability.

  • Demonstrated ability to translate business strategy into learning priorities with measurable impact.

  • Experience working in global, matrixed organizations with senior leaders.

Preferred
  • Experience in commercial real estate, professional services, or complex operational environments.

  • Handson experience with LMS platforms (e.g., Workday Learning), learning analytics, and modern authoring tools.

  • Familiarity with change management and how learning supports transformation initiatives.

Leadership Competencies
  • Strategic, future oriented thinker with strong business acumen

  • Data driven and outcomes focused

  • Highly effective communicator with executive presence

  • Comfortable operating at both strategy and execution levels

  • Collaborative, inclusive leader with a global mindset

  • Calm, organized, and adaptable in fastmoving environments

Why This Role Matters
This role will shape how GOS builds skills for the future, particularly as AI and digital capabilities become core to how we serve clients and operate at scale. The Director, Learning & Development, will play a pivotal role in ensuring our leaders and teams are confident, capable, and prepared to succeed in an evolving landscape.
AAP/EEO Statement:
C&W provides equal employment opportunity to all individuals regardless of their race, color, creed, religion, gender, age, sexual orientation, national origin, disability, veteran status, or any other characteristic protected by state, federal, or local law. Further, the company takes affirmative action to ensure that applicants are employed and employees during employment are treated without regard to any of these characteristics. Discrimination of any type will not be tolerated.
Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and unpaid time away from work. In addition to a comprehensive benefits package, Cushman and Wakefield provide eligible employees with competitive pay, which may vary depending on eligibility factors such as geographic location, date of hire, total hours worked, job type, business line, and applicability of collective bargaining agreements.
The compensation that will be offered to the successful candidate will depend on factors such as whether the position is covered by a collective bargaining agreement, the geographic area in which the work will be performed, market pay rates in that area, and the candidate's experience and qualifications.
The company will not pay less than minimum wage for this role.
The compensation for the position is: $ 136,000.00 - $160,000.00
Cushman & Wakefield is an Equal Opportunity employer to all protected groups, including protected veterans and individuals with disabilities. Discrimination of any type will not be tolerated.
In compliance with the Americans with Disabilities Act Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position at Cushman & Wakefield, please call the ADA line at 1-888-365-5406 or email Accommodations@cushwake.com. Please refer to the job title and job location when you contact us.
INCO: "Cushman & Wakefield"

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