Director of Learning & Development; E&S Segment

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. The company is listed on the NYSE, Fortune 500, S&P 500, with gross written premiums exceeding $10B.

The Berkley brand comprises over 60 businesses worldwide, divided into Insurance & Reinsurance and Monoline Excess. Executive Chairman William R. Berkley and CEO W. Robert Berkley Jr lead the company.

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.

• Develop and lead a comprehensive L&D strategy that supports the E&S segment’s growth, transformation, and talent development goals.
• Apply adult learning principles to design and facilitate interactive, engaging learning experiences that drive knowledge retention and application.
• Coach and develop facilitation capabilities within E&S staff to deliver effective learning sessions.
• Ensure alignment on objectives, shared priorities, and seamless execution of enterprise-developed L&D programs within the E&S segment.
• Design and deliver high-impact professional development programs that strengthen expertise and build a pipeline of ready-now talent for business-critical roles and future leaders.
• 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.
• Support organizational change initiatives through learning interventions that build agility, resilience, and alignment with company values and culture.
• Establish metrics to assess learning effectiveness, business impact, and ROI, using data and feedback to continuously improve programs.

• 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.

• 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.

• Strategic Agility:
  Translates segment strategy into focused learning portfolios and clear outcomes.
• Business Acumen:
  Understands E&S market dynamics and operational drivers.
• 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.
• 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.

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

• Salary Range: $140K to $180K, dependent on experience, knowledge and location.
• Comprehensive employee health benefits:
  Medical, Dental, Vision, FSA, HSA, HRA.
• Retirement and equity: 401(k)/Profit Sharing/ESP, Life/Accidental…