Director of Learning & Development (E&S Segment)

The Company is an equal employment opportunity employer.

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. The 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, ensuring alignment with enterprise-wide learning frameworks while tailoring solutions to segment-specific needs.

• 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.

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

• 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 the company’s values and culture.

• Establish metrics to assess learning effectiveness, business impact, and ROI, using 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 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; 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.
• Capability Building: Demonstrated ability to coach and develop others in facilitation techniques.
• 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: $140,000 to $180,000, dependent on experience, knowledge and location.
• Health benefits: Medical, Dental, Vision, Flexible Spending Account, Health Savings Account, and Health Reimbursement Arrangement.
• Disability and Life Insurance: Short & Long Term Disability, 401(k)/Profit Sharing/Employee Stock Purchase Plan, Life/Accidental Death & Dismemberment/Travel Insurance.
• Paid Time Off: Vacation, Sick, Holidays, and an Employee Assistance Program.
• Wellness and Professional Growth: Employee wellness program, industry-related education and exams, tuition assistance.

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