Top 47 Director learning development Jobs in Chicago Il

Director of Admissions and Enrollment, 2 Hour Learning - $200,000/year USD
Crossover —Chicago, IL
- Full-time
- School experience
- US work authorization
- Senior level
Quick Apply
Talent Development Director
CNA Insurance —Chicago, IL
- $97,000 - $189,000 a year
- Full-time
- Hybrid work
- Organizational skills
- Senior level
- Leadership
Director of Learning & Development
HSO Group B.V. —Chicago, IL
- Remote
- Azure
- Master's degree
- Continuous improvement
- Health insurance
- Dental insurance
Quick Apply
5d
Director, Learning & Development
Brookfield Zoo Chicago —Brookfield, IL
- $139,265 - $154,932 a year
- Weekends as needed
- 5 years
- High school diploma or GED
- Driver's License
- AD&D insurance
- Paid holidays
3d
Director of Agentic Leadership Development
Salesforce —Chicago, IL
- $164,000 - $261,500 a year
- Full-time
- Hybrid work
- Office
- Continuous improvement
- Senior level
- Paid parental leave
- Disability insurance
P&O Director - Digital Capabilities Development
Mars —Chicago, IL
- $242,240 - $333,080 a year
- Full-time
- Hybrid work
- Bachelor's degree
- Psychology
- Mentoring
- Health insurance
- Dental insurance
Director of HR - Learning, Development, and Organizational Effectiveness (In-Office)
Kemper Sports Management LLC —Northbrook, IL
- $110,000 - $130,000 a year
- Full-time
- Office
- 8 years
- Analysis skills
- Dental insurance
- Paid time off
Quick Apply
Director of Organizational Development & Training (HR)
Metropolitan Family Services —Chicago, IL
- $110,000 a year
- Full-time
- Hybrid work
- Office
- 3 years
- Master's degree
- Health savings account
- Health insurance
Quick Apply
AI Transformation & Learning Associate Director
Sidley Austin LLP —Chicago, IL
- $185,000 - $225,000 a year
- Full-time
- Hybrid work
- 7 years
- Analysis skills
- Bachelor's degree
Director of Teaching Innovation and Faculty Development
Chicago State University —Chicago, IL
- Weekends as needed
- 5 years
- Office
- University
- Professional development assistance
14d
Professional Development Director
Million Dollar Round Table —Park Ridge, IL
- $140,000 - $150,000 a year
- Office
- Mentoring
- Contracts
- Health insurance
- Dental insurance
Quick Apply
Senior Director of Monitoring, Evaluation and Learning
The Salvation Army Central Territory —Chicago, IL
- $116,207 - $145,259 a year
- 7 years
- Doctoral degree
- System design
- Disability insurance
- Health insurance
Quick Apply
Director, Attorney AI Learning & Strategy
McDermott Will & Emery —Chicago, IL
- $211,000 - $301,000 a year
- Full-time
- Hybrid work
- Microsoft Excel
- Microsoft Outlook
- Office
Organizational Effectiveness and Change Director
Vizient, Inc. —Chicago, IL
- $102,400 - $179,000 a year
- 7 years
- Microsoft Excel
- Master's degree
Head Director for Early Childhood Learning Center
Little Ayos —Chicago, IL
- $55,000 - $65,000 a year
- Full-time
- Background check
- Classroom
- Spanish
- Health insurance
- Dental insurance
Quick Apply
Learning Center Site Director
Little Angels Learning Center —Chicago, IL
- $25 - $28 an hour
- Full-time
- Background check
- CPR Certification
- Mid-level
- Health insurance
- Paid time off
Quick Apply
HR Director - Global Technology - Chicago, IL
ADM —Chicago, IL
- $174,000 - $270,000 a year
- Overtime
- Background check
- Office
- Master's degree
- Paid parental leave
- Health savings account
Associate Director, Supply Chain - Technical University
Kraft Heinz Company —Chicago, IL
- $164,200 - $205,200 a year
- Weekends as needed
- Hybrid work
- Engineering
- Office
- Travel
- AD&D insurance
- Paid holidays
13d
Director of Scholarship and Career Advancement
Loyola University Chicago —Chicago, IL
- $110,000 - $125,000 a year
- Full-time
- Doctoral degree
- 5 years
- Computer literacy
Associate Director of Legal Practice Technology Team and Knowledge Development
Kirkland and Ellis —Chicago, IL
- $203,000 - $291,000 a year
- Full-time
- Hybrid work
- 7 years
- Residential
- Bachelor's degree
- Health insurance
- Paid time off

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Director of Admissions and Enrollment, 2 Hour Learning - $200,000/year USD

Crossover -
Chicago, IL

Quick Apply

Job Details

Full-time

Qualifications

Client onboarding
Student recruitment
Lead Conversion
Admissions and enrollment management
Client management
Working with families
Sales pipeline management
Consultative selling

Full Job Description

Most admissions roles prioritize volume. This one prioritizes standards.

Alpha is constructing one of the most rigorous school models in the world. Our campuses integrate demanding academics, technology-enabled learning, and elevated expectations for both students and faculty. Students regularly outpace national learning benchmarks, supported by measurable data. Afternoons are structured for depth, autonomy, and practical skill development. The model is effective. But its effectiveness depends on the right families. That is your responsibility.

You will oversee the complete admissions process for a campus, beginning with application and concluding with enrollment. This is not a coordination role. You are accountable for how families perceive us, how accurately they understand the model, and whether enrollment decisions are grounded in the right motivations. You will evaluate alignment, facilitate meaningful dialogue, and recommend "no" when appropriate. The objective is not to maximize enrollment. The objective is alignment.

We welcome candidates from premium service contexts outside of traditional education: selective private schools, competitive programs, luxury hospitality, executive-level support, high-end membership organizations, or entrepreneurs who have personally overseen high-value client experiences from start to finish. What is essential is your capacity to manage a high-touch, multi-phase process with judgment, precision, and accountability. If your career has been defined by delivering white-glove service where trust, discretion, and experience quality are the foundation of the brand, this role will resonate. Apply now to apply that standard to meaningful work.

What you will be doing

Overseeing the complete enrollment experience for prospective families, from initial outreach through onboarding.
Facilitating needs-assessment dialogues to evaluate alignment before presenting options or recommending action.
Tracking 20+ active family relationships across various stages of the enrollment funnel, with precise visibility into progress and follow-up requirements.
Delivering campus tours, shadow day experiences, and decision-stage conversations that transparently convey outcomes, expectations, and model fit.
Ensuring accurate CRM and enrollment data (HubSpot and SIS) to enable forecasting, prioritization, and consistent service delivery.

What you will NOT be doing

Deploying transactional or aggressive sales methods.
Accepting families who do not align with the model in order to meet a quota.
Supervising a large team or navigating complex approval hierarchies.
Distributing responsibility for the family experience across multiple roles.
Operating remotely. This role is on-campus by design.

Key Responsibilities

Own and deliver a high-trust, highly selective enrollment process that secures the right families while safeguarding the integrity and performance of the Alpha model.

Candidate Requirements

3+ years providing premium, personalized service in settings where service quality directly influences brand reputation (education, luxury hospitality, executive support, premium membership organizations, or owner-operated services).
Proven ownership of a complete client, admissions, or enrollment process from initial contact through final onboarding.
Experience managing 20+ client, guest, or family relationships concurrently across different stages, supported by a clear tracking and prioritization system.
Capacity to share specific examples of consultative decision-making, including instances where you recommended against your product or service due to poor fit.
Professional written communication experience with senior executives, high-net-worth individuals, or discerning clients.
Willingness to reside in or relocate within 60 days to one of the following markets: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, or Southlake, TX.
Authorized to work in the United States without visa sponsorship.

Nice to have

Experience in selective private school admissions or enrollment for competitive programs.
Background in luxury hospitality, VIP guest relations, or executive support functions.
Experience developing or refining enrollment workflows, standard operating procedures, or service standards.
Comfort leveraging data and CRM insights to enhance conversion quality, not merely speed.

This position is also known as:

Director of Enrollment Management
Director of Enrollment
Head of Admissions

Quick Apply

Refine Your Search

director learning development jobs in chicago il

Director of Admissions and Enrollment, 2 Hour Learning - $200,000/year USD

Talent Development Director

Director of Learning & Development

Director, Learning & Development

Director of Agentic Leadership Development

P&O Director - Digital Capabilities Development

Director of HR - Learning, Development, and Organizational Effectiveness (In-Office)

Director of Organizational Development & Training (HR)

AI Transformation & Learning Associate Director

Director of Teaching Innovation and Faculty Development

Professional Development Director

Senior Director of Monitoring, Evaluation and Learning

Director, Attorney AI Learning & Strategy

Organizational Effectiveness and Change Director

Head Director for Early Childhood Learning Center

Learning Center Site Director

HR Director - Global Technology - Chicago, IL

Associate Director, Supply Chain - Technical University

Director of Scholarship and Career Advancement

Associate Director of Legal Practice Technology Team and Knowledge Development

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