Director of Learning & Development (E&S Segment)

W. R. Berkley Corporation; Chicago (IL); On-site; USD 140,000 - 180,000; Full time

Benefits offered by this job

Comprehensive health benefits

Flexible Spending Account

Health Savings Account

401(k) with Profit Sharing

Paid Time Off

Job summary

A leading insurance firm located in Chicago is seeking a Director of Learning & Development to enhance employee capability and drive performance through innovative learning solutions. This strategic role requires 7+ years in L&D, proven success in program design, and experience with multi-disciplinary teams. Responsibilities include developing L&D strategies, facilitating impactful learning sessions, and aligning initiatives with business goals. Competitive salary and benefits.

Qualifications

• 7+ years in Learning & Development or Talent Management.
• 5+ years leading multi-disciplinary L&D teams.
• Proven experience designing technical and leadership development programs.
• Experience facilitating learning programs for professionals.

Responsibilities

• Develop and lead a comprehensive L&D strategy.
• Design and facilitate engaging learning experiences.
• Ensure alignment on objectives and shared priorities.
• Design and deliver high-impact professional development programs.
• Identify skill gaps and deliver targeted learning solutions.

Job description

Company Details

“Our Company provides a state of predictability which allows brokers and agents to act with confidence." Founded in 1967, W. R. Berkley Corporation has grown from a small investment management firm into one of the largest commercial lines property and casualty insurers in the United States. Along the way, we’ve been listed on the New York Stock Exchange, become a Fortune 500 Company, joined the S&P 500, and seen our gross written premiums exceed $10 billion. Today the Berkley brand comprises more than 60+ businesses worldwide and is divided into two segments: Insurance and Reinsurance and Monoline Excess. Led by our Executive Chairman, founder and largest shareholder, William. R. Berkley and our President and Chief Executive Officer, W. Robert Berkley, Jr., W.R. Berkley Corporation is well-positioned to respond to opportunities for future growth.

The Company is an equal employment opportunity employer.

Responsibilities

The Director of Learning & Development (L&D) for the E&S segment is a strategic and innovative leader responsible for building and scaling learning solutions that accelerate capability development, drive business performance, and foster a culture of continuous growth. This role partners closely with segment leadership to ensure learning initiatives are tightly aligned with business priorities, talent strategies, and the evolving needs of the E&S marketplace.

Learning Strategy & Execution:

• Develop and lead a comprehensive L&D strategy that supports the E&S segment’s growth, transformation, and talent development goals. Ensure alignment with enterprise-wide learning frameworks while tailoring solutions to segment-specific needs.

Learning Facilitation & Capability Development:

• Apply adult learning principles to design and facilitate interactive, engaging learning experiences that drive knowledge retention and application.
• Build facilitation capability within E&S staff by coaching and developing their skills to deliver effective learning sessions, fostering a culture of knowledge sharing and continuous improvement.

Cross-Segment Collaboration:

• Ensure alignment on objectives, shared priorities, and seamless execution of enterprise-developed L&D programs within the E&S segment. Act as a connector between segment needs and corporate resources.

Professional Development:

• Design and deliver high-impact professional development programs that strengthen expertise and build a pipeline of ready-now talent for business-critical roles as well as future leaders.

Technical & Functional Capability Building:

• Partner with business leaders and SMEs to identify skill gaps and deliver targeted learning solutions that enhance Underwriting, Claims, and other core E&S capabilities.

Change Enablement & Culture Activation:

• Support organizational change initiatives through learning interventions that build agility, resilience, and alignment with company’s values and culture.

Measurement & Impact:

• Establish metrics to assess learning effectiveness, business impact, and ROI. Use data and feedback to continuously improve programs and demonstrate value to stakeholders.

Qualifications

• 7+ years in Learning & Development or Talent Management, with 5+ years leading multi-disciplinary L&D teams and portfolios.
• Proven experience designing, implementing, and scaling technical and leadership development programs with measurable business impact.
• Experience facilitating learning programs for professional audiences and coaching others to become effective facilitators.
• Industry experience in E&S or broader P&C insurance strongly preferred; familiarity with underwriting, claims, and risk disciplines is a plus.
• Demonstrated success partnering with senior business leaders to align learning with strategy and performance goals.
• Established track record of effective partnership with SMEs to develop and execute on program content.
• Experience with learning technologies, data/analytics, vendor selection/management, and program accreditation/certification.

Technical Skills

• Proficiency with LMS/LXP platforms, content authoring tools, learning analytics dashboards, and survey/assessment methodologies.
• Comfort with competency/capability modeling, job architecture, career frameworks, and instructional design best practices.

Skills & Competencies

• Strategic Agility: Translates segment strategy into focused learning portfolios and clear outcomes.
• Business Acumen: Understands E&S market dynamics and operational drivers; ties learning to performance and risk outcomes.
• Program Design Excellence: Crafts blended, scalable solutions with strong pedagogy and applied practice.
• Facilitation Expertise: Skilled in applying adult learning theory to create dynamic, learner-centered experiences. Able to engage diverse audiences and adapt delivery methods for maximum impact.
• Capability Building: Demonstrated ability to coach and develop others in facilitation techniques, fostering a culture of knowledge sharing and continuous improvement.
• Stakeholder Influence: Aligns diverse leaders and functions; manages ambiguity and competing priorities effectively.
• Data-Driven Decision-Making: Uses analytics to prioritize, iterate, and demonstrate ROI.
• Change Leadership: Orchestrates learning that enables adoption, resilience, and behavioral shift.
• Inclusive Leadership: Builds equitable access to learning; promotes diverse pipelines and psychological safety.
• Operational Discipline: Delivers with quality, timeliness, and fiscal responsibility.
• Accountability: Resourceful, self-sufficient and takes full ownership of results.

Education Requirment

• Bachelor’s degree required; Master’s degree in HR, Education, Organizational Psychology, Business, or related field preferred

Additional Company Details

Salary Range - $140K to $180K, dependent on experience, knowledge and location. Berkley is committed to offering comprehensive and competitive employee health benefits that help our employees stay healthy, feel secure and maintain a work/life balance. We offer Medical, Dental, Vision, Flexible Spending Account, Health Savings Account and a Health Reimbursement Arrangement. We support our employees in planning for their current and future security by offering Short & Long Term Disability, 401(k)/Profit Sharing/Employee Stock Purchase Plan, Life/Accidental Death & Dismemberment/Travel and Additional Life Insurance. We want our employees to live productive and fulfilling lives. We promote work-life balance and personal wellness by providing an Employee Assistance Program, Paid Time Off (Vacation/Sick/Holidays) and encouraging employees to participate in our groups wellness program. We take risk management excellence and your professional growth and ongoing development seriously by offering industry-related education and exams along with industry-related tuition assistance.