Commercial Lines Underwriting Training Supervisor

About us

Good things are happening at Berkshire Hathaway GUARD Insurance Companies. We provide Property & Casualty insurance products and services through a nationwide network of independent agents and brokers. Our companies are all rated A+ “Superior” by AM Best (the leading independent insurance rating organization) and ultimately owned by Warren Buffett’s Berkshire Hathaway group – one of the financially strongest organizations in the world!

Headquartered in Wilkes-Barre, PA, we employ over 1,000 individuals and have offices across the country. Our vision is to be the leading small business insurance provider nationwide.

Founded upon an exceptional culture and led by a collaborative and inclusive management team, our company’s success is grounded in our core values: accountability, service, integrity, empowerment, and diversity. We are always in search of talented individuals to join our team and embark on an exciting career path!

• Competitive compensation
• Healthcare benefits package that begins on first day of employment
• 401K retirement plan with company match
• Enjoy generous paid time off to support your work‑life balance plus 9 ½ paid holidays
• Up to 6 weeks of parental and bonding leave
• Hybrid work schedule (3 days in the office, 2 days from home)
• Longevity awards (every 5 years of employment, receive a generous monetary award to be used toward a vacation)
• Tuition reimbursement after 6 months of employment
• Numerous opportunities for continued training and career advancement

The Underwriting Training Supervisor is responsible for designing, delivering, and overseeing training programs that enhance technical proficiency, decision‑making, and compliance of commercial insurance underwriters. This role ensures that new and existing underwriting staff are equipped with the knowledge and skills necessary to assess risk accurately, adhere to company guidelines, and contribute to profitable growth.

• Training Program Development
  • Design and implement onboarding and continuing education programs for underwriters.
  • Collaborate with underwriting leadership to identify skill gaps and training needs.
  • Develop curriculum covering underwriting principles, risk assessment, policy forms, regulatory compliance, and systems usage for core products.
• Instructional Delivery
  • Facilitate live and virtual training sessions using adult learning principles.
  • Coach underwriters on training and facilitation skills, technical aptitude, decision‑making, and documentation standards.
  • Provide one‑on‑one mentoring and support for new hires and underperforming staff.
• Performance Monitoring & Evaluation
  • Assess training effectiveness through evaluations, audits, and performance metrics.
  • Collaborate with underwriting leaders to monitor trainee progress and provide feedback.
  • Continuously improve training materials based on training feedback and industry changes.
• Collaboration & Communication
  • Work closely with peers, Product teams, and across the organization to ensure training aligns with business goals and regulatory requirements.
  • Serve as a subject matter expert on underwriting best practices and systems.

• Bachelor’s degree in Business, Insurance, Education or related field or equivalent knowledge and experience.
• 3+ years of underwriting experience, with strong knowledge of property and casualty lines.
• 2+ years of experience in training, coaching, or instructional design.
• CPCU or AU designation preferred.
• Excellent communication, facilitation, and interpersonal skills.
• Proficiency in Microsoft Office and virtual training platforms.

• Experience with adult learning theory and instructional design models (e.g., ADDIE).
• Ability to translate complex underwriting concepts into engaging learning experiences.
• Strong communication and analytical skills, with an attention to detail.
• Leadership and influence across cross‑functional teams.

55, USD per year. The annual base salary range posted represents a broad range of salaries around the U.S. and is subject to many factors including but not limited to credentials, education, experience, geographic location, job responsibilities, performance, skills and/or training. The successful candidate is expected to work in one of our offices 3 days per week and also be available for travel as required.

• Mid‑Senior level

• Full‑time

• Human Resources

• Insurance