Underwriting Careers at Industry Leaders

Discover your next underwriting adventure with friends of Kalepa and leaders in commercial insurance

Underwriting Trainee - Remote or Hybrid

Paragon Insurance Holdings

Paragon Insurance Holdings

Oregon, USA · Remote
Posted on Tuesday, May 14, 2024

Why Paragon? In 2014, Paragon was incepted in a Starbucks coffee shop with a simple strategy — build the MGA that we would want to work for. Years later, Paragon is one of the fastest growing MGAs in the country. Our secret? A dedication to diversity and agility. We realized from the start that a commitment to thinking, acting, and rewarding “different” would resonate within the industry. It is hard to argue with results, and the results are clear. Our diverse team of talent is reshaping an industry that has weathered “boring” and is long overdue on “different.” Whether it comes by offering better pay, benefits or growth opportunities, we will continue to aggressively invest in talent to drive our business forward. Change is here, come be a part of it with us.

About the job

In today’s complex risk environment, public entities need a team of experienced and dedicated experts on their side. The team at Trident Public Risk Solutions is uniquely qualified to meet these challenges head-on, with over 30 years in the public entity sector that’s backed by the strength of our A-rated or better carrier partners. Using traditional and creative approaches, Trident can offer a wide range of solutions to meet the needs of Public Entities. Our Underwriters take a lead role in evaluating, selection and pricing risk. This opportunity provides broad insurance experience on a wide variety of exposures related to the cities, counties, school and special districts we insure!

The goal of the Trainee Program is to prepare the trainee for promotion to Underwriter. The length of time in Trainee Status depends on the individual, their ability to learn and apply concepts reviewed throughout the trainee program. Typically, this can range between 6 months to 18 months depending on the individual.

The Underwriting Trainee will work remotely with availability to do occasional travel or a hybrid schedule in our Avon, CT offices.


  • Continuously develop and strengthen the skills required for success in the underwriting position to prepare for additional responsibility.
  • Plan and prioritize work activities to achieve desired results within necessary time frames.
  • Develop strong customer service skills (consistency, quick response, knowledge of products)
  • Learns to use independent judgment and initiative to support business goals.
  • Observe and work with Underwriters and Underwriting Leaders to become familiar with the functions of this position.
  • Use business acumen to gather and review information on risk exposure, loss history, and economic trends that may impact the terms and conditions offered.
  • Learn to review applications for completeness, request appropriate underwriting requirements and document pertinent details.
  • Develop proficiencies in internal systems and processes that support the task of underwriting.
  • Successfully completes the training program, having demonstrated an ability to make independent and sound underwriting decisions
  • Develop and maintain positive and productive relationships with Underwriting Management, Underwriters, Underwriting Assistants, and Strategic Operations.
  • Participate in projects as assigned.
  • Takes responsibility for own actions and decisions.


  • College degree in Risk Management, Insurance or related field and/or 1 to 3 years of general insurance experience.
  • Proficient with Microsoft Word, Excel and Paragon/Trident Systems. Excellent communication skills, both verbal and written.
  • Strong organizational, interpersonal and communication skills.
  • Ambitious career minded candidates with a strong financial aptitude and outstanding people skills for a professional career.

Ready to have your voice heard, your talents properly utilized and to become a valued part of a rapidly growing organization? You’re in the right place.

Paragon is a dynamic, bold, and tenacious company. Join us as we continue to chart new paths, open doors and grow together.

Paragon is an Equal Opportunity Employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin or citizenship status, sexual orientation, gender identity or expression, pregnancy, marital or familial status, disability status, medical condition, genetic information, military or veteran status, political affiliation, or any other characteristic protected by law. We are committed to fostering a work community where every colleague feels welcomed, valued, respected and heard, as we believe that that creating an environment where every employee feels included and empowered, helps us to deliver the best outcome to our clients.