Underwriting Training & Development Manager

Berkley • Hamilton Square, NJ

11d • Hybrid

About The Position

This role will be based in our Hamilton Square, NJ or West Hartford, CT office. We offer a hybrid work schedule with 4 days in the office; and 1 day remote where it makes sense to do so. The Stop Loss Underwriting Training & Development Manager is a newly created role focused on strengthening Berkley Accident & Health’s underwriting talent pipeline and supporting consistent training, mentorship, operational excellence, and quality assurance across the underwriting enterprise. We'll trust you to lead onboarding, training, mentorship, and career development programs for Underwriting Analysts and early‑career Underwriters within the Employer Stop Loss segments (both Traditional and Group Captive). You will partner closely with Underwriting management to drive continuous improvement initiatives, help maintain and enhance underwriting guidelines, and contribute to the underwriting quality assurance (QA) framework. The ideal candidate is an experienced underwriting professional who is passionate about developing others while also playing a key role in shaping our operational practices. This individual will design and deliver structured training programs, lead mentorship efforts, support guideline maintenance, enhance quality controls, and ensure Underwriters have the tools and knowledge needed to advance into more complex underwriting roles.

Requirements

• Bachelors’ degree in business, finance, insurance or related field.
• Prior experience designing and implementing training programs.
• Leadership experience within underwriting or insurance operations.
• 7+ years of experience in medical stop loss underwriting or a related insurance discipline.
• Proven ability to train, mentor, and develop underwriting or analytical talent.
• Strong communication, facilitation, and presentation skills with the ability to engage diverse audiences.
• Excellent organizational and project management skills.
• Proficiency in the Microsoft Office Suite

Nice To Haves

• Strong relationship‑building and collaboration skills across cross‑functional teams.
• Innovative mindset with a focus on improving processes and enhancing the employee experience.
• Familiarity with underwriting systems (e.g., Connexure) preferred.
• Demonstrated passion for talent development, operational excellence, and continuous improvement.

Responsibilities

• Develop and manage a comprehensive onboarding program for new Underwriting Analysts.
• Create and deliver training modules covering underwriting principles, risk assessment, systems, tools, and operational processes.
• Maintain and update training materials to reflect current guidelines, product changes, and best practices.
• Establish and oversee a formal mentorship program pairing Analysts and early career Underwriters with more experienced, senior level Underwriters.
• Provide ongoing coaching, feedback, and skill development guidance.
• Monitor individual progress and identify opportunities for additional training or targeted support.
• Design clear career development pathways from Analyst through Senior Analyst and into junior underwriting roles.
• Partner with HR and Underwriting leadership to ensure training programs align with organizational goals and compliance standards.
• Gather and evaluate feedback from training participants, mentors, and managers to strengthen program effectiveness.
• Collaborate with underwriting leadership, claims, actuarial, finance, sales, and other functional partners to ensure training supports business needs.
• Coordinate Analyst summits, workshops, and skills‑based breakout sessions to drive engagement and collaboration.
• Oversee the underwriting file audit process, including guideline adherence, authority compliance, pricing tool usage, and documentation standards.
• Identify trends, recurring deficiencies, and opportunities for process improvement.
• Partner with Underwriting leadership to refine policies, procedures, tools, and training content based on audit insights.
• Prepare periodic audit reports for senior management, including quality findings, remediation actions, and completion status.
• Lead projects that advance underwriting operational efficiency, automation, and standardization efforts.

Benefits

• competitive compensation
• paid time off
• comprehensive wellness benefits and programs
• employer funded health savings account
• generous profit sharing
• 401k
• paid parental leave
• employee stock purchase plan
• tuition assistance and professional continuing education
• Health, Dental, Vision, Life, Disability, Wellness, Paid Time Off, 401(k) and generous Profit-Sharing plans.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level