Specialty Underwriting Trainee **2026

This is a hybrid position requiring 3 days in office at our Hartford, CT or Middleton, WI office location.

At CapSpecialty, we are a specialty underwriting company being driven by well-informed, entrepreneurial and proactive employees. Come join our exciting company where you can really make an impact, and each individual's unique skills and talents are recognized and valued. You will find an accessible leadership team that welcomes opinions and ideas. We owe much of our success to our collaborative environment and set of three guiding principles rooted in customer-centricity, employee excellence and corporate culture.

We offer competitive compensation and benefits packages – including an innovative open vacation plan, generous paid sick and parental leave, fully vested matching 401k, company-paid group term life insurance and short- & long-term disability plans, professional and educational growth opportunities, flexible and casual work environment, and recognition for exceptional performance. Please see our full list of Total Rewards here.

CapSpecialty is seeking college graduates for a year-long Underwriting Training program to begin in June 2026. Candidates who successfully complete the program will become Underwriters. The program will include hands on training within one or two underwriting units, in addition to time spent with various department heads and leaders across the company to learn more about insurance operations, the history of CapSpecialty, how insurance companies generate profits and the role of reinsurance. During the program, trainees will learn the basics of how to underwrite specialty lines insurance, analyze financial statements, interpret a policy form and interact with CapSpecialty’s wholesale broker partners. Additional training will encompass negotiation skills, presentation skills and decision-making skills. Participation in department meetings, roundtables, monthly business reviews (MBRs), Joint Accountability Groups (JAGs) and large claim meetings will be a critical component of the program. Trainees will spend time with Actuarial, Marketing & Engagement, Claims and Portfolio Management during their training, in addition to accompanying members of the underwriting team on marketing visits. Formal performance evaluations will occur at three, six, nine and 12 months. The Underwriting Training program is designed to provide candidates with the knowledge and skills required to begin a successful underwriting career.

Duties/Responsibilities

• Candidates will become immersed in the insurance principles they learn so that they have a basic understanding of how to evaluate a risk and can move into a production role upon completion of the Underwriting Training program.
• Candidates will apply underwriting analysis on actual accounts to support production underwriters.
• Candidates will begin to develop relationships with their assigned brokers.
• Candidates will perform other duties as needed.
  
  

Supervisory Responsibilities

None.

Core Competencies

• Superior oral and written communication skills coupled with sales skills and an ability to develop relationships with brokers.
• Skilled in the use of personal computers, the internet and multiple software applications and programs.
• Ability to work independently, problem solve and meet deadlines while also working on a team as a team player.
• Strong organizational skills with an attention to detail.
  
  

Education And Experience

• Bachelor’s degree from an accredited college.
• Previous office experience helpful.
  
  

Physical Demands

• Prolonged periods of sitting at a desk and working on a computer.
• May be required to lift up to 15 lbs. at times.
• May require business travel up to 15%.
  
  

CapSpecialty is a leading provider of specialty insurance and bonds for small- to mid-sized businesses in the U.S., offering casualty, professional liability, surety and fidelity products in all 50 states and the District of Columbia. By working with select partners through a limited distribution model, CapSpecialty's creative, hard-working team provides personalized service and cultivates mutually successful partnerships to deliver positive results. CapSpecialty is an operating subsidiary of Berkshire Hathaway, and its carriers have an A ("Excellent") rating from A.M. Best, writing both admitted and non-admitted policies. For more information, please visit CapSpecialty.com.

Apply today!

Equal Employment Opportunity Employer