Underwriting Training & Development Manager

Company Details

Berkley Accident and Health is a risk management company that designs innovative solutions to address the unique challenges of each client. With our entrepreneurial culture and a strong emphasis on analytics, we can help employers better manage their risk. We offer a broad range of products, including employer stop loss, benefit captives, provider stop loss, HMO reinsurance, and specialty accident. The key to Berkley’s success is our nimble approach to risk – our ability to quickly understand, think through, and devise a plan that addresses each client’s challenges, coupled with the strong backing of a Fortune 500 company. Our parent company,  W. R. Berkley Corporation , is one of the largest and best managed property/casualty insurers in the United States.

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The Company is an equal employment opportunity employer.

Responsibilities

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.

What you can expect:

• Culture of innovation, teamwork, supportive colleagues and leaders willing to invest in talent
• Internal mobility opportunities 
• Visibility to senior leaders and partnership with cross functional teams
• Opportunity to impact change
• 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

We'll count on you for:

Onboarding & Training

• 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.

Mentorship & Development

• 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.

Program Design & Continuous Improvement

• 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.

Cross‑Team Collaboration

• 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.

Quality Assurance & Underwriting Guideline Maintenance

• 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.

Qualifications

What you need to have:

• 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

What makes you stand out:

• 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.

Additional Company Details

We do not accept any unsolicited resumes from external recruiting agencies or firms. The company offers a competitive compensation plan and robust benefits package for full time regular employees which for this role include: • Base Salary Range: $130,000 to 150,000 • Eligible to participate in annual discretionary bonus. • Benefits: Health, Dental, Vision, Life, Disability, Wellness, Paid Time Off, 401(k) and generous Profit-Sharing plans. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment.

Sponsorship Details

Sponsorship not Offered for this Role