Director Underwriting Learning & Enablement

About Us

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.

Overview

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.

Responsibilities

• Enterprise Learning Strategy & Architecture: 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
• Learning Delivery Innovation: 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.
• Business-Driven Knowledge Gap Identification: 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
• Training Effectiveness & Outcome Measurement: 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.
• Regional Standardization & Influence: 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
• Content Alignment with LOB Technical Teams: 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
• Communication Strategy for 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
• Trainee & Early Career Programs: 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.
• Technology & Tool Enablement: 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
• Team Leadership & Trainer Development: 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.
• Must be available during working hours for eastern standard time. 

Qualifications

Knowledge and 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

Education and Experience

•College degree required; Degree in Instructional Design, Education, Organizational Development, or related field preferred
•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)
•CPCU, AU, CPLP, or other relevant professional designations preferred

Total Rewards

Selective Insurance offers a total rewards package that includes a competitive base salary, incentive plan eligibility at all levels, and a wide array of benefits designed to help you and your family stay healthy, achieve your financial goals, and balance the demands of your work and personal life. These benefits include comprehensive health care plans, retirement savings plan with company match, discounted Employee Stock Purchase Program, tuition assistance and reimbursement programs, and 20 days of paid time off. Additional details about our total rewards package can be found by visiting our benefits page.  

The actual base salary is based on geographic location, and the range is representative of salaries for this role throughout Selective's footprint. Additional considerations include relevant education, qualifications, experience, skills, performance, and business needs.

Pay Range

USD $163,000.00 - USD $211,000.00 /Yr.
Additional Information

Selective is an Equal Employment Opportunity employer. That means we respect and value every individual’s unique opinions, beliefs, abilities, and perspectives. We are committed to promoting a welcoming culture that celebrates diverse talent, individual identity, different points of view and experiences – and empowers employees to contribute new ideas that support our continued and growing success. Building a highly engaged team is one of our core strategic imperatives, which we believe is enhanced by diversity, equity, and inclusion. We expect and encourage all employees and all of our business partners to embrace, practice, and monitor the attitudes, values, and goals of acceptance; address biases; and foster diversity of viewpoints and opinions.

For Massachusetts Applicants

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.