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Training and Development Manager

Location
Chicago, IL
Work type
Full Time ยท On-site
Posted
2026-09-01

Job description

Key Responsibilities
Learning & Development
Develop and execute the corporate Learning & Development strategy.
Design technical training programs for Underwriters and other business functions.
Develop leadership development programs for managers and future leaders.
Create onboarding and new hire learning curriculums.
Establish a blended learning approach including instructor-led training, e-learning, coaching, mentoring, and experiential learning.
Manage external training providers, consultants, and educational partnerships.

Underwriting Development Programs
Build underwriting career ladders and development frameworks.
Establish underwriting competency models for all levels.
Develop underwriting academies, certification pathways, and technical excellence programs.
Partner with business leaders to identify capability gaps and training priorities.
Coordinate mentoring, job shadowing, and stretch assignment opportunities.

Leadership Development
Design and administer leadership development programs for emerging leaders, managers, and senior leaders.
Develop leadership competencies aligned with HDI's business strategy.
Facilitate management training in: Coaching & Feedback, Change Leadership, Strategic Thinking, Performance Management, Communication & Influence, Talent Development, Others
Support executive coaching and leadership assessments.

Talent Assessment & Succession Planning
Lead enterprise succession planning processes.
Identify critical roles and succession candidates.
Facilitate talent review discussions and calibration sessions.
Implement leadership potential and readiness assessments.
Build talent pipelines for future leadership needs.
Develop Individual Development Plans (IDPs) for high-potential employees.
Track succession readiness and bench strength metrics.

Career Pathing & Workforce Development
Design career paths and career progression frameworks across business functions.
Maintain career ladders for underwriting and other key disciplines.
Support employee career planning discussions.
Provide guidance on skills development and advancement opportunities.
Align career growth opportunities with organizational workforce planning needs.

Program Measurement & Analytics
Measure training effectiveness and learning outcomes.
Track employee development, internal promotions, and succession metrics.
Monitor leadership pipeline health and bench strength.
Develop reporting for senior leadership and Board reviews.
Recommend improvements based on workforce analytics and business outcomes.

Qualifications
Bachelor's Degree in Human Resources, Organizational Development, Education, Business, or related field.
Master's Degree preferred.
10+ years of Learning & Development, Talent Management, Organizational Development, or HR leadership experience.
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.

Competencies
Leadership Development
Adult Learning Theory
Talent Management
Succession Planning
Organizational Development
Assessment & Talent Analytics
Change Management
Executive Coaching
Stakeholder Management
Project & Program Management

Success Measures
Increased internal promotion rates.
Successful succession coverage for critical roles.
Improved leadership bench strength.
Higher employee engagement and retention.
Increased completion of development programs.
Improved underwriting capabilities and technical competency.
Positive manager and employee feedback regarding career development opportunities.

This role effectively combines Learning & Development, Talent Management, Leadership Development, and Succession Planning into one strategic function focused on building HDI's future underwriting and leadership talent pipeline.

Compensation and Benefits:
Base salary range for this position is $145,000 โ€“ 160,000, plus eligibility for a performance-based annual bonus. Actual compensation will be based on a variety of factors including experience, education, and location. We offer a competitive benefits package, including: 401(k) with company match, Paid Time Off, Sick Leave, Medical, Health Reimbursement Arrangement (HRA), Telemedicine, Wellness Program, Employee Assistance Program (EAP), Dental, Vision, Accident & Critical Illness Insurance, Flexible Spending Account (FSA), Dependent Care FSA, Group and Voluntary Life Insurance, Short- and Long-Term Disability, Pet Insurance, Transit and Parking benefits.

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