Director of Learning & Development (E&S Segment)

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 weve 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.

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 segments 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 companys 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.

• 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

• Bachelors degree required; Masters degree in HR Education Organizational Psychology Business or related field preferred