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Remote Underwriter Trainee Jobs in Connecticut (NOW HIRING)

PLADS Group Underwriter III

Shelton, CT · On-site +1

$90K - $120K/yr

If the role is remote, there may be occasions that you are requested to come to the office based on ... Solid Group Life/Disability underwriting knowledge * Understanding of Group Life and Disability ...

Underwriter-IM

Hartford, CT · On-site +1

$67K - $110K/yr

Imagine loving what you do and where you do it. Job Category Underwriting Compensation Overview The annual base salary range provided for this position is a nationwide market range and represents a ...

Senior Analyst, Underwriter

Farmington, CT · On-site +1

$46K - $112K/yr

This role prefers a hybrid presence in CT, though remote applicants will also be considered. #AetnaUW Required Qualifications : - 3+ years of experience in underwriting pricing methodologies and ...

Cyber and Tech Risk UW SR

Hartford, CT · On-site +1

$99K - $117K/yr

Position will be Remote - US based About the Role The Senior Cyber & Technology Risk Underwriter is responsible for underwriting transactional Cyber and Technology Errors & Omissions risks while ...

This role partners closely with underwriting, product, actuarial, and technology leaders to deliver ... This role can have a Hybrid or Remote work schedule. Candidates who live near one of our office ...

Remote Underwriter Trainee information

What is a remote underwriter trainee?

A Remote Underwriter Trainee is an entry-level professional who is learning how to assess and evaluate loan, insurance, or mortgage applications while working from a remote location. Trainees receive on-the-job training under the supervision of experienced underwriters to learn industry regulations, risk assessment, and decision-making processes. They typically review applicant information, verify documentation, and apply company guidelines to determine eligibility. This position is ideal for those seeking to enter the underwriting field and gain foundational experience before advancing to more independent roles.

What are the key skills and qualifications needed to thrive as a remote underwriter trainee, and why are they important?

To thrive as a Remote Underwriter Trainee, you need a foundational understanding of risk analysis, attention to detail, and typically a bachelor’s degree in finance, business, or a related field. Familiarity with underwriting software, loan origination systems, and relevant industry certifications such as AUS (Automated Underwriting System) are commonly required. Strong analytical thinking, effective communication, and self-motivation are important soft skills for excelling in a remote environment. These skills and qualifications are crucial for accurately assessing risk, ensuring compliance, and contributing to efficient, high-quality underwriting decisions from a remote setting.

What are some common challenges faced by remote underwriter trainees and how can they be addressed?

Remote Underwriter Trainees often encounter challenges such as adapting to complex underwriting software, interpreting risk assessments without in-person guidance, and managing communication with distributed teams. To overcome these, it's important to proactively seek mentorship from experienced underwriters, participate in virtual training sessions, and utilize collaboration tools to maintain clear, consistent communication. Developing strong organizational skills and asking questions during team meetings can also help trainees quickly adapt and build confidence in their role.

What is the difference between Remote Underwriter Trainee vs Remote Underwriter?

AspectRemote Underwriter TraineeRemote Underwriter
Required CredentialsEntry-level, often with a relevant degree or certificationTypically requires experience and professional certifications
Work EnvironmentTraining period, supervised, learning-focusedFull responsibilities, independent decision-making
Job ResponsibilitiesAssisting in underwriting tasks, learning processesEvaluating applications, making underwriting decisions

The main difference between a Remote Underwriter Trainee and a Remote Underwriter is the experience level and responsibilities. Trainees are in learning mode, focusing on training and support, while underwriters handle full underwriting duties independently. Both roles are common in insurance and financial industries, with the trainee position serving as a stepping stone to becoming a fully qualified underwriter.

Infographic showing various Remote Underwriter Trainee job openings in Connecticut as of August 2026, with employment types broken down into 87% Full Time, 9% Part Time, 2% Temporary, and 2% Contract. Highlights an 98% Physical, 1% Hybrid, and 1% Remote job distribution.

Cyber Underwriter - West Coast (Remote)

Hartford, CT • On-site, Remote

Full-time

Medical, Life, Retirement, PTO

Re-posted 14 days ago


Job description

HSB, a Munich Re company, is a specialty insurer and risk solutions provider focused on cyber and technology risk. We combine underwriting expertise, cyber risk intelligence, and advanced analytics to help organizations anticipate, prevent, and mitigate evolving digital threats. Our cyber offerings are supported by proactive risk management services and data-driven insights designed to strengthen operational resilience and reduce loss-putting prevention at the center of cyber insurance.
This position is a Remote opportunity.
About the role
The Cyber & Technology Risk Underwriter I is responsible for underwriting transactional Cyber and Technology Errors & Omissions risks while supporting the growth and profitability of the cyber portfolio. This role partners closely with agents, brokers, and internal business development teams to expand the book of business, provide market insight in a rapidly evolving segment, and support product, coverage, and rate initiatives. The position also plays a key role in supporting alternative distribution channels and strategic partnerships.
Key Responsibilities
  • Underwrite new business, renewals, and endorsements for Cyber and Technology E&O risks
  • Quote, rate, bind, and issue policies, including interim policy changes throughout the policy lifecycle
  • Support execution of short- and long-term underwriting and portfolio objectives
  • Monitor, evaluate, and recommend improvements to underwriting processes for direct cyber products and MGA partnerships
  • Provide market insight and recommend coverage or rate changes based on evolving cyber risk trends
  • Collaborate internally to implement product, coverage, and pricing updates
  • Manage marketing efforts and track cyber-related client management activities
  • Partner with internal business development teams and external agents to drive new business
  • Meet with internal stakeholders and external partners to educate and train on cyber products
  • Ensure audit compliance and adherence to underwriting guidelines, standards, and authority levels

Qualifications
  • Bachelor's degree in Risk Management, Marketing, Computer Science, Engineering, or a related discipline, or equivalent work experience
  • Three or more years of experience in the insurance and/or reinsurance industry
  • One or more years of cyber liability underwriting experience preferred
  • Experience in commercial underwriting and/or insurance marketing
  • Experience in Cyber, Technology E&O, or Management Liability (carrier or consulting environment preferred)
  • IT or cybersecurity-related experience preferred
  • CPCU, RPLU, or other relevant insurance designation preferred

Knowledge & Skills
  • Strong analytical and problem-solving abilities
  • Excellent organizational and time-management skills
  • Strong interpersonal and relationship-building capabilities
  • Ability to collaborate effectively across teams and stakeholders
  • Solid understanding of insurance concepts and underwriting principles
  • Strong verbal and written communication skills

At The Hartford Steam Boiler, a subsidiary of Munich Re, we see Diversity and Inclusion as a solution to the challenges and opportunities all around us. Our goal is to foster an inclusive culture and build a workforce that reflects the customers we serve and the communities in which we live and work. We strive to provide a workplace where all of our colleagues feel respected, valued and empowered to achieve their very best every day. We recruit and develop talent with a focus on providing our customers the most innovative products and services.
We are an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status. The work environment characteristics, and any physical and mental requirements described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
This job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee. Other duties, responsibilities and activities may change or be assigned at any time with or without notice.
The Company is open to considering candidates in numerous locations, including California. The salary ranged posted below applies to the Company's Hartford, CT location.
• The salary range for this position is $ 84,500 - $124,000, plus opportunity for company bonus. In addition, the company provides a variety of benefits to employees, including health insurance coverage, an employee wellness program, life and disability insurance, a retirement savings plan, paid holidays and paid time off (PTO).
• The salary estimate displayed represents the typical salary range of candidates hired. Factors that may be used to determine your actual salary may include your specific skills, how many years of experience you have and comparison to other employees already in this role. Most candidates will start in the bottom half of the range