Description

Position Title: Risk Manager Contractor
Accountable To: Board of Directors
Location: Wisconsin-based position. Hybrid work arrangement available. Frequent statewide travel to member districts and events is required. 
Contract Type: Independent Contractor Agreement, typical 20-30 hours/week

WERMC is a cooperative of 70 Wisconsin school districts and CESAs with a 25-year history of providing innovative risk management solutions. Through a strong focus on risk prevention and loss control, WERMC helps members reduce liability, workers' compensation, property, and cyber losses while creating safer environments for students, staff, and communities.  Our vision is to be the premier provider of risk management solutions for Wisconsin's education community, continually seeking ways to enhance the safety and success of educators and students. We aim to foster a culture of risk awareness and responsibility within the education community.

Position Overview: Due to the planned retirement of the current Dedicated Consultant, WERMC is seeking an Independent Contractor to serve as the chief executive officer of the Property/Liability/Workers' Compensation/Cyber Insurance Cooperative. The Independent Contractor will provide strategic leadership, operational management, and oversight of all cooperative activities. This individual is responsible for advancing the organization's mission, ensuring financial sustainability, fostering stakeholder engagement, and overseeing the delivery of high-quality insurance and risk management services tailored to member organizations' needs. 

Mission: Our mission is to proactively identify, assess, and mitigate potential risks affecting the Wisconsin education community, while seeking opportunities to enhance members' resilience and success. We strive to cultivate a culture of risk awareness and responsible decision-making, and to provide expert guidance and support. 

Vision: Our vision is to be the premier provider of risk management solutions for Wisconsin's education community, continually seeking ways to enhance the safety and success of educators and students. We aim to foster a culture of risk awareness and responsibility within the education community. 

Motto: Leading the Way in Risk Management for Wisconsin’s Education Community.

Strategic Leadership:

Develop and execute the cooperative’s strategic vision and long-term goals in alignment with the Board of Directors’ directives.
Monitor industry trends and regulatory changes to ensure the cooperative remains competitive and compliant.
Identify and evaluate new opportunities for growth, partnerships, and service enhancement.
Identify emerging risks and develop mitigation strategies to protect the cooperative and its members. 
Operational Management:

Oversee day-to-day operations. 
Ensure the effective delivery of insurance lines, including but not limited to: property, liability, cyber and workers' compensation.
Develop and manage the annual budget to guarantee financial transparency and accountability.
Drive the insurance renewal process and provide expert guidance.
Develop and oversee communication strategies, including emails, newsletters, surveys, and meeting agendas, to ensure clear, consistent, and effective messaging.
Plan, organize, and oversee professional development for members.
Develop and implement strategies to drive membership growth, enhance brand awareness, and support the organization's long-term strategic expansion.
Conduct in-person visits with members to build relationships, understand their needs, and strengthen engagement, fostering long-term collaboration and trust. Other duties as assigned by the Board of Directors.

Risk Management:

Evaluate and educate members about the risks associated with insurance coverage, claims management, and the impact on individual district operations.
Recommend policies and procedures to members to ensure safeguards are in place to protect assets.
Provide expert consulting services to members, offering guidance and solutions. 
Stakeholder Engagement:

Act as a relationship manager between the cooperative and external partners.
Actively recruit new members to the cooperative.
Communicate regularly with the Board of Directors, providing updates on operational performance, strategic initiatives, and emerging challenges.
Coordinate and support board committee operations.
Keep abreast of advocacy emerging trends pertaining to insurance needs.
Program Development and Oversight:

Ensure the cooperative’s insurance programs meet the unique needs of member organizations, offering competitive rates, comprehensive coverage, and superior customer service.
Work with members on an advisory level to manage and resolve claims issues.
Continuously evaluate and improve member services based on feedback and industry best practices.

Education:

A relevant degree or equivalent professional experience in a related field is required.
Experience:

Understanding the unique challenges and opportunities within K-12 education.
Experience developing and implementing programs or services for K-12.
Demonstrated experience with School Risk Management.
Knowledge of the insurance industry, with expertise in property, liability, cyber and workers' compensation insurance.
Demonstrated success in managing insurance programs, risk management, or cooperative models.
Experience working with a Board of Directors and managing governance processes.
Compensation:

Initial three-year contract, with the opportunity for renewal or extension upon mutual agreement of the contractor and Board of Directors. 
This Independent Contractor Agreement is for an estimated 20-30 hours per week. The initial term of this contract is three years, with the option to renew or extend upon mutual agreement between the contractor and the Board of Directors.

How to Apply: Interested candidates should submit their resume, cover letter, and three professional references to Brian Adesso ([email protected]) by July 10, 2026.

We are an Equal Opportunity Employer and consider all qualified applicants without regard to race, color, religion, sex, national origin, age, disability, or any other legally protected status."

Requirements

Evaluate and educate members about the risks associated with insurance coverage, claims management, and the impact on individual district operations.
Recommend policies and procedures to members to ensure safeguards are in place to protect assets.
Provide expert consulting services to members, offering guidance and solutions. 
Stakeholder Engagement:

Act as a relationship manager between the cooperative and external partners.
Actively recruit new members to the cooperative.
Communicate regularly with the Board of Directors, providing updates on operational performance, strategic initiatives, and emerging challenges.
Coordinate and support board committee operations.
Keep abreast of advocacy emerging trends pertaining to insurance needs.
Program Development and Oversight:

Ensure the cooperative’s insurance programs meet the unique needs of member organizations, offering competitive rates, comprehensive coverage, and superior customer service.
Work with members on an advisory level to manage and resolve claims issues.
Continuously evaluate and improve member services based on feedback and industry best practices.