Systems Trainer Jobs in Wisconsin (NOW HIRING)

The Commercial Lines Trainer is responsible for developing, delivering, and continuously improving training for Commercial Lines team members to ensure consistent best practices in servicing, maintaining, expanding, and retaining Commercial Lines accounts. This role serves as a subject matter expert for coverages, workflows, and systems, with a strong emphasis on onboarding, EPIC system training, and integration of newly acquired offices.

The Commercial Lines Trainer works closely with Regional Commercial Lines Leadership and cross-functionally with Mergers & Acquisitions, Operations, and other internal partners to ensure seamless integration, adoption of standards, and a high-quality customer experience. We are hiring for one position, but this position can be based out of any of our Ansay locations in Wisconsin. 

• Train and onboard Commercial Lines Account Managers, Account Executives, and Producers on core responsibilities, workflows, coverage fundamentals, and best practices

• Serve as a primary point of contact during onboarding for new hires and newly integrated teams

• Design and lead Commercial Lines training programs, including live training sessions, webinars, presentations, and lunch-and-learn events aligned with departmental goals

• Provide ongoing coaching, guidance, and feedback through auditing, monitoring, and performance reviews in partnership with department leadership

• Support all Commercial Lines acquisitions by leading EPIC system integration, workflow alignment, and training of incoming team members

• Actively participate in book consolidations and special projects related to acquisitions and evolving business needs

• Collaborate cross-departmentally with Mergers & Acquisitions, Operations, and leadership teams to ensure smooth transitions and consistency across regions

• Maintain expert-level knowledge of EPIC Agency Management System capabilities and updates

• Train and support both new and existing staff on system enhancements, workflows, and technology adoption

• Identify workflow gaps, coverage issues, and training opportunities through hands-on servicing and auditing

• Recommend and implement improvements to reduce E&O exposure and enhance efficiency and service quality

• Maintain and proactively manage an assigned book of Commercial Lines business in accordance with agency standards

• Educate clients on coverage, identify gaps, and recommend solutions to meet business needs

• Support account retention through best-in-class service and proactive communication

• Cross-sell additional lines of business and collaborate with other departments when appropriate

• Stay current on industry trends, carrier changes, products, and regulatory updates

• Participate in ongoing training and pursue professional designations to enhance technical expertise

• Bachelor’s degree in Business or a related field (or equivalent experience)

• Thorough understanding of Commercial Lines insurance products, coverages, and servicing workflows

• Active insurance license in accordance with state requirements

• At least one professional insurance designation (CISR, CIC, CRM, or similar), or willingness to obtain

• Self-starter with strong initiative and a continuous improvement mindset

• Excellent communication, presentation, and relationship-building skills

• Strong attention to detail and active listening skills

• Ability to collaborate effectively across teams and regions

• Customer-focused with a commitment to service excellence

• Team-oriented with a positive, solution-driven attitude

At Ansay, we believe our people are our greatest advantage. As a growing, employee-focused insurance agency with deep roots in the communities we serve, we are committed to investing in our team members’ success, development, and well-being.

We offer a collaborative and supportive culture where expertise is valued, ideas are welcomed, and continuous improvement is encouraged. With ongoing growth through organic expansion and strategic acquisitions, Ansay provides meaningful opportunities to make an impact, develop professionally, and help shape the future of our organization.

• Competitive compensation aligned with experience and performance

• Comprehensive benefits package including medical, dental, vision, life, and disability insurance

• 401(k) retirement plan with company match

• Generous paid time off and paid holidays

• Opportunities for professional development, training, and insurance designation support

• Career growth opportunities within a growing, multi-regional organization

• Collaborative, team-oriented culture with leadership support

• Technology-forward environment with ongoing system enhancements and training

At Ansay, you’ll be empowered to grow your career while delivering best-in-class service to clients and supporting teammates across the organization.