Top 45 Director of learning and development Jobs in Chicago, Il

Director of Enrollment Management, 2 Hour Learning - $200,000/year USD
Crossover —Chicago, IL
- Full-time
- Remote
- School experience
- US work authorization
- Senior level
Quick Apply
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
Director of Agentic Leadership Development
Salesforce —Chicago, IL
- $164,000 - $261,500 a year
- Full-time
- Hybrid work
- Office
- Continuous improvement
- In-person
- Paid parental leave
- Disability insurance
Director of Teaching Innovation and Faculty Development
Chicago State University —Chicago, IL
- Weekends as needed
- 5 years
- Office
- University
- Professional development assistance
7h
Director, Agentic Leadership Growth & Succession
Salesforce —Chicago, IL
- $164,000 - $261,500 a year
- Full-time
- Hybrid work
- Office
- Presentation skills
- In-person
- Paid parental leave
- Disability insurance
Director, Customer Enablement & Learning
Applied Systems, Inc. —Chicago, IL
- $140,000 - $175,000 a year
- Full-time
- Remote
- 5 years
- Senior level
- Leadership
- 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
5d
P&O Director - Digital Capabilities Development
Mars —Chicago, IL
- $242,240 - $333,080 a year
- Full-time
- Bachelor's degree
- Psychology
- Mentoring
- Health insurance
- Dental insurance
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, 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
Director of Attorney Professional Development
Akerman LLP —Chicago, IL
- $180,000 - $220,000 a year
- Full-time
- Bachelor's degree
- Continuous improvement
- Travel
- Profit sharing
- Paid holidays
Quick Apply
Talent Development Director
CNA Insurance —Chicago, IL
- $97,000 - $189,000 a year
- Full-time
- Hybrid work
- Organizational skills
- Senior level
- Leadership
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
FW 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
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
6d
Director of Human Resources/Compliance
Angel Of God Resource Center —Chicago, IL
- Full-time
- Office
- Bachelor's degree
- Recruiting
- Health insurance
- Dental insurance
Quick Apply
13d
Director of Sales Training - High Ticket
Curvion Blue —Chicago, IL
- $120,000 - $150,000 a year
- Full-time
- Remote
- Senior level
- Teaching
- Analytics
Quick Apply
Human Resources Director
Roderick MacArthur Foundation —Chicago, IL
- $130,000 - $155,000 a year
- Hybrid work
- Microsoft Excel
- Microsoft Outlook
- Data analysis skills
- Disability insurance
- Health insurance
Quick Apply
6d

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

Crossover -
Chicago, IL

Quick Apply

Job Details

Full-time

Qualifications

Client onboarding
Lead Conversion
Admissions and enrollment management
Client management
Lead Tracking
Working with families

Full Job Description

Many enrollment positions prioritize volume. This position prioritizes standards.

Alpha is constructing a school model that ranks among the most ambitious globally. Our campuses integrate rigorous academics with technology-enabled learning and maintain elevated expectations for both students and educators. Student learning velocity consistently exceeds national benchmarks, supported by measurable data. Afternoons are allocated to depth work, independent learning, and practical skill development. The model is effective. Its effectiveness, however, depends entirely on enrolling the right families. That responsibility is yours.

You will control the entire admissions process for a campus, beginning with the application and concluding with enrollment. This is not a role with fragmented ownership. You are accountable for the family experience, the clarity with which they understand our model, and the soundness of their enrollment decision. You will evaluate compatibility, facilitate substantive dialogue, and advise against enrollment when appropriate. The objective is not to maximize enrollment figures. The objective is to ensure alignment.

We welcome candidates whose backgrounds include premium service delivery outside conventional education: selective private schools, competitive programs, upscale hospitality, executive assistance, exclusive membership organizations, or entrepreneurial operators who have directly managed high-value client experiences from start to finish. What counts is your capacity to execute a sophisticated, multi-phase process with discernment, precision, and accountability. If your career has been defined by delivering exceptional service where trust, discretion, and experiential quality constitute the brand, this role will resonate. Apply now to apply that standard to meaningful work.

What you will be doing

Controlling the complete enrollment experience for prospective families, spanning initial contact through onboarding completion.
Facilitating needs-assessment discussions to establish fit prior to introducing solutions or advising on subsequent actions.
Overseeing 20+ concurrent family engagements across various enrollment stages, maintaining transparent tracking and follow-up protocols.
Directing campus visits, shadow day experiences, and decision-oriented conversations that articulate outcomes, expectations, and model suitability with clarity.
Ensuring precise CRM and enrollment documentation (HubSpot and SIS) to enable forecasting accuracy, prioritization, and service excellence.

What you will NOT be doing

Employing transactional or aggressive sales methodologies.
Admitting families who do not align with the model solely to achieve enrollment targets.
Overseeing a sizable team or operating within complex hierarchical approval structures.
Distributing responsibility for the family journey across multiple staff members.
Performing this work remotely. This position requires on-campus presence by design.

Key Responsibilities

Own and deliver a high-trust, selective enrollment process that successfully converts well-aligned families while safeguarding the integrity and outcomes of the Alpha model.

Candidate Requirements

3+ years providing premium, tailored service in settings where service excellence directly influences brand perception (education, upscale hospitality, executive assistance, exclusive membership, or owner-operated services).
Proven ownership of a complete client, admissions, or enrollment process from initial engagement through onboarding.
Experience concurrently stewarding 20+ client, guest, or family accounts across varying stages, supported by a reliable tracking and prioritization framework.
Capacity to furnish specific examples of consultative judgment, including instances where you advised against your product or service due to poor fit.
Professional-grade written communication experience with senior leadership, high-net-worth clients, or discerning stakeholders.
Willingness to reside in or relocate within 60 days to one of these locations: Chicago, IL, Nashville, TN, Oklahoma City, OK, Tulsa, OK, or Southlake, TX.
Authorization to work in the United States without requiring visa sponsorship.

Nice to have

Experience in competitive private school admissions or selective program enrollment processes.
Professional history in upscale hospitality, VIP client services, or executive-level assistance.
Experience designing or refining enrollment workflows, standard operating procedures, or service protocols.
Proficiency leveraging data and CRM analytics to enhance conversion quality, not merely velocity.

This position is also known as:

Director of Admissions and Enrollment
Director of Admissions
Head of Admissions

Quick Apply

Refine Your Search

director of learning and development jobs in chicago, il

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

Head Director for Early Childhood Learning Center

Learning Center Site Director

Director of Agentic Leadership Development

Director of Teaching Innovation and Faculty Development

Director, Agentic Leadership Growth & Succession

Director, Customer Enablement & Learning

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

P&O Director - Digital Capabilities Development

AI Transformation & Learning Associate Director

Director, Attorney AI Learning & Strategy

Organizational Effectiveness and Change Director

Director of Attorney Professional Development

Talent Development Director

Senior Director of Monitoring, Evaluation and Learning

FW Associate Director of Legal Practice Technology Team and Knowledge Development

Professional Development Director

Director of Human Resources/Compliance

Director of Sales Training - High Ticket

Human Resources Director

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