Director of Learning & Development (E&S Segment)
About The Position
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.
Requirements
- 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.
- 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; 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.
- Bachelor’s degree required
Nice To Haves
- Industry experience in E&S or broader P&C insurance strongly preferred; familiarity with underwriting, claims, and risk disciplines is a plus.
- Master’s degree in HR, Education, Organizational Psychology, Business, or related field preferred
Responsibilities
- 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.
- 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.
- 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.
- 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’s values and culture.
- Establish metrics to assess learning effectiveness, business impact, and ROI.
Benefits
- Medical
- Dental
- Vision
- Flexible Spending Account
- Health Savings Account
- Health Reimbursement Arrangement
- Short & Long Term Disability
- 401(k)/Profit Sharing/Employee Stock Purchase Plan
- Life/Accidental Death & Dismemberment/Travel and Additional Life Insurance
- Employee Assistance Program
- Paid Time Off (Vacation/Sick/Holidays)
- Wellness program
- Industry-related education and exams along with industry-related tuition assistance
Stand Out From the Crowd
Upload your resume and get instant feedback on how well it matches this job.
What This Job Offers
Job Type
Full-time
Career Level
Director
Number of Employees
5,001-10,000 employees
