Director Underwriting Learning & Enablement (Hybrid)

Selective Insurance Company of America•Short Hills, NJ

8d•Hybrid

About The Position

At Selective, we don't just insure uniquely, we employ uniqueness. Selective is a midsized U.S. domestic property and casualty insurance company with a history of strong, consistent financial performance for nearly 100 years. Selective's unique position as both a leading insurance group and an employer of choice is recognized in a wide variety of awards and honors, including listing in Forbes Best Midsize Employers in 2025 and certification as a Great Place to Work® in 2025 for the sixth consecutive year. Employees are empowered and encouraged to Be Uniquely You by being their true, unique selves and contributing their diverse talents, experiences, and perspectives to our shared success. Together, we are a high-performing team working to serve our customers responsibly by helping to mitigate loss, keep them safe, and restore their lives and businesses after an insured loss occurs. Leads the enterprise underwriting learning and enablement function, owning the strategy, governance, and continuous improvement of training programs that develop underwriting capabilities and drive business results. Oversees onboarding, trainee, technical, technology, and change-related learning initiatives; leverages performance data to address skill gaps; and partners across the organization to align learning with underwriting strategy, standards, and evolving business needs. Responsible for building and scaling the learning function to support underwriting, premium audit, risk management, and technology enablement. All duties and responsibilities must be performed in compliance with applicable legal and regulatory requirements.

Requirements

Demonstrated leadership experience in learning and development within insurance or financial services, expertise in adult learning and learning technologies, and strong analytical, communication, and stakeholder management skills.
Experience driving training effectiveness, leading teams, and knowledge of P&C underwriting operations are preferred.
Valid driver's license and ability to travel required
College degree required
10+ years of experience in corporate learning, training, instructional design, or talent development — preferably within P&C insurance or financial services
5+ years of leadership/management experience overseeing learning teams and strategic training programs
5+ years of experience in P&C insurance underwriting or underwriting operations strongly preferred
Experience designing learning programs across multiple delivery modalities (classroom, eLearning, video, AI-enabled, virtual)

Nice To Haves

Degree in Instructional Design, Education, Organizational Development, or related field preferred
CPCU, AU, CPLP, or other relevant professional designations preferred

Responsibilities

Designs and owns the enterprise learning architecture for underwriting — a comprehensive framework that defines how knowledge is structured, sequenced, delivered, assessed, and refreshed across all lines of business, segments, and career levels. Ensures the architecture is scalable, adaptable, and aligned with the company's strategic direction. Continuously evaluates and evolves the learning strategy to incorporate emerging trends, technologies, and best practices in adult education and corporate learning
Determines the most effective delivery method for each learning need by maintaining deep expertise in adult learning theory and modern instructional approaches. Evaluates and deploys a range of modalities including AI-generated content, interactive simulations, video-based instruction, knowledge checks, eLearning modules, virtual instructor-led training, and traditional classroom sessions. Ensures delivery methods are matched to learning objectives, audience needs, and scalability requirements.
Leverages underwriting performance data, QA results, Focus review findings, loss trends, authority compliance reporting, and other business metrics to proactively identify knowledge gaps across the organization. Translates data insights into targeted learning interventions that directly address performance issues and drive measurable improvement toward business outcomes
Designs and implements a rigorous framework for assessing training effectiveness — moving beyond satisfaction surveys to measure knowledge retention, behavioral change, and business impact. Establishes success metrics tied to underwriting quality, profitability, consistency, and operational outcomes.
Leads the effort to standardize training practices across all regions, ensuring a consistent enterprise learning experience. Works through influence rather than direct authority to align regional training approaches, eliminate inconsistencies, and establish enterprise-wide standards for content delivery, assessment, and program execution. Partners with regional leadership to balance standardization with regional flexibility where appropriate
Ensures seamless collaboration with LOB Technical teams (Casualty and Property) who create curricula and technical training content. Takes LOB-originated content and translates it into professionally designed, pedagogically sound learning experiences. Ensures all training content is current, aligned with the authoritative guideline source of truth, and updated promptly when guidelines, workflows, or tools change
Develops and owns the communication strategy for notifying underwriting staff of any changes to content, workflows, or guidelines that affect how they do their work. Ensures communications are timely, clear, and delivered through the most effective channels. Coordinates with Governance, LOB Technical, IT, and Operations to ensure nothing reaches the field without appropriate training and communication support
Oversees the Momentum Trainee program and onboarding programs, ensuring they provide a strong foundation for new underwriting professionals. Designs the strategic roadmap for expanding early career development programs — including structured rotational experiences, mentorship frameworks, and progressive skill-building curricula. Plans for future expansion into premium audit training, risk management training, and technology-specific enablement programs.
Partners on the training and communication strategy for all vendor tools, underwriting systems, and technology deployments that impact underwriting workflows. Engages with LOB Technical teams, Product and Operations to ensure effective training accompanies technology change. Evaluates and manages the Learning Management System and supporting technologies to maximize delivery capability and learner experience
Leads, develops, and mentors the Learning & Enablement team, including the Training Program Leader, Learning Management Specialist, and Learning Technology Specialist. As staffing allows, sources and develops dedicated full-time trainers to expand delivery capacity. Builds a high-performing team culture centered on instructional excellence, innovation, business alignment, and continuous improvement. Manages the department budget and vendor relationships