Jobs › Kemper

Director, Learning and Development

Kemper · Chicago, IL · $111,900–$186,700 a year · Full time

Posted Oct 2, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a management development program you designed. How did you know it worked?

What they are checking: Whether they measure real behavior and performance change, not just attendance or satisfaction.

Tell me about a time you had to shift a learning culture that wasn't working.

What they are checking: Whether they can drive cultural change and continuous learning at scale.

How do you lead and grow your own L&D team?

What they are checking: Whether they practice the development they're asking the rest of the company to adopt.

What would you do

How would you scale development across locations like Chicago, Dallas and Birmingham plus remote employees?

What they are checking: Whether they can design learning that works for a distributed workforce consistently.

How do you get senior leaders to sponsor and actually participate in learning programs?

What they are checking: Whether they can influence executives and make development part of the business, not an HR side project.

You have a limited budget and three business units each want a major program. How do you decide?

What they are checking: Whether they prioritize by business impact and can explain tradeoffs to leaders.

How would you build learning for frontline managers who are busy and skeptical of training?

What they are checking: Whether they design for real working conditions so managers actually engage.

About the work

How would you build an enterprise learning strategy that supports a specialized insurer's business priorities?

What they are checking: Whether they start from business needs and future capabilities, not from a catalog of courses.

How do you decide whether a performance problem is actually a training problem?

What they are checking: Whether they can tell skill gaps apart from process, incentive or leadership issues.

What's your view on using AI and digital tools in corporate learning?

What they are checking: Whether they can use new technology thoughtfully to make learning scalable and relevant.

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The full job description

As published by Kemper.

Location(s) Birmingham, Alabama, Chicago, Illinois, Dallas, Texas, P&C-Butterfield Road-Downers Grove-IL-AAC Details Kemper is one of the nation’s leading specialized insurers. Our success is a direct reflection of the talented and diverse people who make a positive difference in the lives of our customers every day. We believe a high-performing culture, valuable opportunities for personal development and professional challenge, and a healthy work-life balance can be highly motivating and productive. Kemper’s products and services are making a real difference to our customers, who have unique and evolving needs. By joining our team, you are helping to provide an experience to our stakeholders that delivers on our promises. Position Summary: Responsible for shaping and executing Kemper’s enterprise-wide learning and development strategy in alignment with our culture and business priorities. Leads the design and delivery of scalable, innovative, and impactful development solutions that accelerate performance, strengthen management capability, and foster a culture of continuous learning across all levels of the organization. Position Responsibilities: • Responsible for the development of a cohesive end-to-end enterprise management and professional development learning strategy that aligns with Kemper’s strategic objectives, culture, and future capabilities. • Develop and oversee the design and implementation of progressive, scalable learning frameworks that integrate modern adult learning theory, learning technologies, and blended delivery methodologies. • Serve as a trusted advisor and internal consultant to leaders and HR partners by partnering to identify learning needs and translating them into actionable development strategies that drive performance. Partner with the Talent Management, Talent Acquisition, and Business HR teams to ensure integrated development strategies that enhance career progression and productivity. • Manage and develop a team of high performing L&D professionals to meet the Talent Solutions Team’s objectives while fostering collaboration, innovation, and professional growth. • Responsible for the delivery of key enterprise learning programs and facilitate sessions as needed. Ensure curriculum relevance, engagement, and alignment with business priorities. • Lead optimization of the Workday Learning module for enterprise-wide adoption, learning curation, and data-driven decision making. • Owns the mechanisms that evaluate program effectiveness, learning transfer, and ROI; use data insights to continuously enhance learning solutions. • Lead a community of practice with other L&D leaders across the organization to develop consistent practices and share knowledge. Position Qualifications: • Education: Bachelor’s degree in Learning and Development, Organizational Development, or another related field strongly preferred. • Experience: At least 10 years of progressive experience in learning and development, organizational development, or talent management. • At least 5 years in a leadership role managing enterprise L&D strategy and execution. • Strong experience with people management including team building experience. • Proven expertise in adult learning theory, instructional design, management development, and organizational learning. • Demonstrated success designing and delivering enterprise-scale development programs with measurable business impact. • Strong business acumen and experience aligning learning strategy with organizational goals and capabilities. • Experience with Workday Learning and related HCM systems a plus; familiarity with leveraging learning data and analytics to drive improvement. • Exceptional communication, facilitation, and stakeholder management skills; comfortable influencing and engaging senior leadership. • Project and change management experience in complex, matrixed environments. Additional Information: • Up to 15% travel • Sponsorship is not accepted for this position. • This role can be worked hybrid out of Kemper’s Chicago, IL, Downers Grove, IL, Birmingham, AL or Richardson, TX office. The range for this position is $111,900 to $186,700. When determining candidate offers, we consider experience, skills, education, certifications, and geographic location among other factors. This job is eligible for an annual discretionary bonus and Kemper benefits (Medical, Dental, Vision, PTO, 401k, etc.) Kemper is proud to be an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, disability status or any other status protected by the laws or regulations in the locations where we operate. We are committed to supporting diversity and equality across our organization and we work diligently to maintain a workplace free from discrimination. Kemper is focused on expanding our Diversity, Equity and Inclusion efforts to align with our vision, mission, and guiding principles. Kemper does not accept unsolicited resumes through or from search firms or staffing agencies. All unsolicited resumes will be considered the property of Kemper and Kemper will not be obligated to pay a placement fee. Kemper will never request personal information, such as your social security number or banking information, via text or email. Additionally, Kemper does not use external messaging applications like WireApp or Skype to communicate with candidates. If you receive such a message, delete it.

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