Underwriter Trainee

Penn National InsuranceWaukesha, WI
$52,313 - $71,930Remote

About The Position

Penn National Insurance is hiring an Underwriter Trainee who is a closely supervised, entry-level employee in which the incumbent obtains an understanding of surety and fidelity underwriting through both a formal and on-the-job training. Within limited authority, the incumbent demonstrates the ability to effectively perform the assignments of an underwriter. Upon the successful completion of training, the Underwriter Trainee is a candidate for future positions within the Home Office. This is a remote position, with the preferred candidate residing in Iowa, Wisconsin, or Minnesota.

Requirements

  • Minimum of an associate’s degree required.
  • This is an entry level position.
  • Good math and accounting aptitude
  • Good research, analytical and problem-solving skills
  • Good oral and written communication skills
  • Good inter-personal skills
  • Good customer service skills
  • Good PC skills, with an emphasis on Microsoft Office Suite
  • Must be a self-starter, with an ability to learn
  • Must be highly organized with a good attention to detail
  • This position is primarily a sedentary position that requires occasional standing and walking throughout the office environment.
  • Must be able to perform computer-based tasks and access digital information necessary for job duties, including through the use of assistive technologies.
  • Must be able to complete computer-based tasks and utilize office equipment as needed to perform essential job functions.
  • Must be able to access and enter information accurately using automated systems.
  • Must be able to communicate effectively with internal and external clients using telephone, electronic, or other communication systems.
  • Must be able to present information to individuals and groups.
  • Must be able to interpret and apply concepts that may or may not be based upon established guidelines.
  • Must be able to maintain acceptable attendance and adhere to scheduled work hours.
  • Must have a valid driver’s license and be able to operate a motor vehicle.
  • Must be able to travel, with overnight stays required.

Responsibilities

  • Initiates purposeful contact with those who have the knowledge and influence to advance work goals; focuses on contacts who share mutual interests.
  • Research and resolve business issues, prepare management reports and other projects under the direction of the leader.
  • As training progresses, performs basic underwriting duties on non-complex and complex accounts.
  • Allocates appropriate amounts of time for completing own and others’ work; avoids scheduling conflicts; develops timelines and milestones.
  • Uses time effectively and prevents irrelevant issues or distractions from interfering with work completion.
  • Looks for and communicates the positive qualities and longer-term benefits of challenging situations.
  • The main function of this position is to successfully complete and apply knowledge and skills developed during formal classroom and/or on-the-job training sessions, as set forth in a defined training schedule.
  • Must have a willingness to pursue and complete professional education courses as required.
  • Within Surety and Fidelity, analyzes financial statements and work-in-progress reports, reviews contracts and bond forms, and performs credit background checks.
  • Performs other duties as may be assigned by the Vice President, Surety and Fidelity.

Benefits

  • Generous 401(k) match
  • graded profit sharing
  • incentive compensation
  • a wide range of benefits to support your financial health, physical well-being and career development.
  • remote and hybrid work options
  • flexible scheduling
  • a “dress-for-your-day” culture.
  • Continuing Education Support
  • 100% tuition reimbursement for academic studies.
  • Professional Development Opportunities
  • Tailored designation programs to help you advance in your career such as CPCU, AINS, CPA, CISSP, and more.
© 2026 Teal Labs, Inc
Privacy PolicyTerms of Service