The Middle Market Trainee, working under direct supervision, is responsible to acquire knowledge, experience, skills, and business acumen in the assigned area such as Claims, Surety, IT, etc. The role completes educational, work, and relationship building experiences and participates and engages in all assignments/experiences, soliciting feedback regarding performance, and closing gaps in his/her knowledge, skills, and business acumen. In addition, the role also establishes a strong foundation by building relationships and identifying resources that will help them in their career.
Job Responsibilities
Works to acquire the knowledge, experience, skills, and business acumen in the assigned area, which helps in the trainee's development towards the goal of becoming a professional in the respective department.
Assists leader, team, or business unit with work assigned to them.
This often includes, but is not limited to, project work and coverage of day-to-day activities.
Develops business acumen through interactions and shadowing with other professionals.
Attends business unit meetings, executes research, and creates and delivers presentations as assigned.
Prepares for and engages in one-on-one, on-line, and on-the-job learning/educational assignments/ experiences.
Develops operating knowledge of Company standardized hardware, software programs, third-party software, and processing procedures.
Works toward developing an understanding of key concepts and appropriate business skill application through learning programs, structured on the job experiences, and active participation and engagement in all team building, observation and practice activities.
Solicits reinforcing and constructive feedback from leader, peer coaches and others in the organization and incorporates feedback into development.
Identifies resources, best practices, and external networking opportunities to monitor pertinent industry activity and trends.
Maintains awareness, understanding, and compliance with internal policies and procedures, laws, and regulations appropriate for this position.
Job Qualifications
High School Diploma or General Education Diploma (GED) and/or commensurate experience.
Bachelor's degree in Risk Management, Finance, or Business preferred.
Location
Hybrid - defined as working three or more days per week in the office. Potential relocationafter Trainee program is complete.
Start Date
June 2026
Behavioral Competencies
Collaborates
Customer focus
Communicates effectively
Decision quality
Nimble learning
Technical Skills
Business Analysis
Data Management
Data Entry
Insurance Operations
Insurance Policies
Insurance Industry Knowledge
Information Systems
Data Analysis and Reporting
This job description describes the general nature and level of work performed in this role. It is not intended to be an exhaustive list of all duties, skills, responsibilities, knowledge, etc. These may be subject to change and additional functions may be assigned as needed by management.
Westfield was founded in 1848 by a small group of hard-working farmers who believed in the promise of the future and the power of the individual. Originally called Ohio Farmers Insurance Company, we became known as Westfield in 1971. While our name may have changed, we remain true to our founders’ vision.
Our unique approach to insurance services allows us to deliver value beyond the policy. We are known not only for our longevity and stability, but also our distinct blend of technology and human connection, superior claims experience, and insights that help customers and clients understand and manage risks.
Westfield has grown from a grassroots insurance company in Ohio to a leading U.S.-based property and casualty insurance company. We provide personal insurance in 9 states, commercial insurance in 21 states, and surety products in 50 states through a vast network of independent insurance agents. Westfield Specialty currently offers 11 lines of business insurance in the U.S., nine in the U.K., and five in Dubai.
