Senior Learning & Leadership Development Manager

HDI; Chicago, Northern (IL, KY); Hybrid; USD 145,000 - 160,000; Full time

Benefits offered by this job

401(k) match

PTO

Sick leave

Medical insurance

Health Reimbursement Arrangement (HRA)

Telemedicine

Wellness program

Employee Assistance Program (EAP)

Dental

Vision

Disability insurance (short & long)

Life insurance

FSA (Health/Dependent Care)

Transit benefits

Parking

Job summary

HDI Global Insurance Company in Chicago, IL, seeks a Training and Development Manager to design and lead enterprise-wide learning and talent development initiatives. This role focuses on building underwriting capability, strengthening leadership, and creating career paths and succession pipelines for critical roles.

Partnering with senior leadership, the role drives programs across the organization, measuring impact and aligning development with business goals to support sustainable growth and

Qualifications

• Bachelor’s degree in HR, Organizational Development, Education, Business, or related field.
• Master’s Degree preferred.
• 10+ years in Learning & Development, Talent Management, Organizational Development, or HR leadership.
• Experience developing leadership and management programs.
• Experience leading succession planning and talent review processes.
• Experience supporting professional and technical career development frameworks.
• Insurance experience strongly preferred.

Responsibilities

• Design and lead enterprise-wide Learning & Development strategy.
• Develop leadership development programs for managers and future leaders.
• Build underwriting career ladders and development frameworks.
• Establish underwriting competency models for all levels.
• Develop onboarding and new hire learning curriculums.
• Coordinate mentoring, job shadowing, and stretch assignments.
• Partner with leaders to identify capability gaps and training priorities.
• Measure training effectiveness and report outcomes.

Skills

Leadership Development

Talent Management

Succession Planning

Organizational Development

Executive Coaching

Stakeholder Management

Project & Program Management

Change Management

Adult Learning Theory

Assessment & Talent Analytics

Education

Bachelor’s Degree in HR/OD/EDU/Business

Master’s Degree preferred

Job description

HDI Global Insurance Company in Chicago, IL, seeks a Training and Development Manager to design and lead enterprise-wide learning and talent development initiatives. This role focuses on building underwriting capability, strengthening leadership, and creating career paths and succession pipelines for critical roles.

Partnering with senior leadership, the role drives programs across the organization, measuring impact and aligning development with business goals to support sustainable growth and