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Remote Underwriter Trainee Jobs in Boston, MA (NOW HIRING)

Leader Bank

Underwriter

Arlington, MA · On-site +1

$65K - $98K/yr

The Underwriter will demonstrate knowledge of the mortgage industry and assist with planning and reporting in accordance with Leader Bank, compliance with federal laws, corporate standards and ...

GEICO

Auto Damage Trainee (Field)

Boston, MA · On-site +1

This is not a remote role; you will be required to work in the territory listed on the job posting ... Valid driver's license that meets company underwriting guidelines required. * Core Skills: * Strong ...

All JobsUnderwriter JobsRemote Underwriter Trainee JobsRemote Underwriter Trainee Jobs in Boston, MA

Remote Underwriter Trainee information

See Boston, MA salary details

$35.3K

$85.7K

$151.6K

How much do remote underwriter trainee jobs pay per year?

As of Aug 25, 2026, the average yearly pay for remote underwriter trainee in Boston, MA is $85,694.00, according to ZipRecruiter salary data. Most workers in this role earn between $66,300.00 and $94,500.00 per year, depending on experience, location, and employer.

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.

What are popular job titles related to Remote Underwriter Trainee jobs in Boston, MA?

For Remote Underwriter Trainee jobs in Boston, MA, the most frequently searched job titles are:

What job categories do people searching Remote Underwriter Trainee jobs in Boston, MA look for?

The top searched job categories for Remote Underwriter Trainee jobs in Boston, MA are:

Remote Underwriter Trainee jobs near you
Infographic showing various Remote Underwriter Trainee job openings in Boston, MA as of August 2026, with employment types broken down into 89% Full Time, 9% Part Time, and 2% Contract. Highlights an 96% Physical, 2% Hybrid, and 2% Remote job distribution, with an average salary of $85,694 per year, or $41.2 per hour.

Senior Underwriter, Structured Solutions - Remote

Boston, MA • On-site, Remote

Trisura Guarantee Insurance Company
See more jobs at Trisura Guarantee Insurance Companyexternal

$107K - $126K/yr

Full-time

Medical, Dental, Vision, Retirement

Posted 28 days ago

Job description

At Trisura, we expect more because we believe it can be done better.
Trisura brings innovative solutions and expertise through a select network of both national and regional brokerage firms in the commercial insurance space.
Trisura is a growth-oriented team with a commitment to attracting and retaining exceptional talent. Our growth has awarded us accolades, and our entrepreneurial style and niche market position ensure that our people see the results of their hard work reflected in the company's success. As our organization continues to grow, we are investing in enterprise-wide process maturity, system governance, and delivery excellence to support scalable and compliant operations.
Senior Underwriter - Structured Solutions
Remote - USA
Reporting to the Executive Vice President, Structured Solutions, the successful candidate will be a passionate, results-driven underwriter with the experience and vision to grow our Structured Solutions portfolio. Working in close collaboration with our ceded reinsurance, legal, client relations, finance and claims teams, you will evaluate and execute program opportunities from end to end. You will play a key role in developing underwriting guidelines, procedures, and policy language, building rating plans, and providing strategic oversight of a growing book of business.
As an integral member of the team, you will bring:
  • 10+ years of commercial underwriting experience with a focus on multi-line portfolio management.
  • Strong communication, relationship management, organizational and analytical skills, with a demonstrated ability to manage a portfolio of business.
  • Familiarity with rating and policy issuance platforms, with the ability to quickly learn and adapt to proprietary systems.
  • Working knowledge of ISO, admitted and non-admitted product execution.
  • Proven understanding of manuscript and admitted form language, including policy coverage analysis.
  • Demonstrated ability to leverage analytical tools, data reports and underwriting technology.
  • The ability to thrive in a dynamic, fast-paced environment, adapting quickly, collaborating broadly and delivering solutions under pressure.
  • Flexibility, a willingness to learn on the job, and a positive, can-do attitude.
  • A highly motivated, results-oriented mindset with a proven track record as a creative problem solver.
  • Excellent verbal and written communication skills.
  • Willingness to travel approximately 30% of the time.

Responsibilities include:
  • Preparing underwriting review documents and summaries for presentation to senior management for each assigned program, including plans for new business, renewal rate management, and expected retentions, all designed to position the division to meet its profit objectives.
  • Participating in underwriting reviews and conducting additional file reviews as needed.
  • Leveraging data and analytics to actively manage all programs and drive profitability through consistent monitoring of renewals, rate targets, retentions, trends, and lost business, on a monthly basis.
  • Developing a thorough understanding of each assigned program, including the relevant industries, their loss exposures, and any needed updated to program eligibility and coverage terms, in order to minimize unanticipated adverse exposures.
  • Proactively identify training opportunities at the Program Administrator level to strengthen line-of-business knowledge, and guiding Program Administrators in risk selection, pricing, coverage terms and conditions in alignment with authorities granted by Trisura.
  • Demonstrating a clear understanding of industry changes and their potential impact by line-of-business, and providing well-articulated recommendations during the account referral process.
  • Ensuring Program Administrator meet Trisura's underwriting expectations and remain aligned with business plans through active management of underwriting guidelines, file reviews, and client relations meetings.
  • Collaborating with Actuarial, Finance, Claims, Operations, Compliance, Systems, and Legal teams as required.
  • Developing and maintaining strong working relationships with Program Administrators through regular on-site visits, conference calls, and overseeing the onboarding and implementation of new programs.
  • Leading new program opportunity due diligence reviews and overseeing the onboarding and implementation of new programs.
  • Successfully managing the renewal of current program relationships on an annual basis.

If you are looking for a career at an exciting and rewarding company, driven to excel, thriving in a team environment, and eager to contribute to an organization that truly values your input, we want to hear from you!
We thank all candidates for their interest, however, only those selected for an interview will be contacted.
Here at Trisura, we are committed to an inclusive and barrier-free workplace that reflects diversity. Accommodation will be provided on request for candidates taking part in all aspects of our recruitment and selection process. All qualified applications will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identify, national origin, disability or protected veteran status.
The salary range is expected to be $175,000 to $200,000 plus bonus, based on geographical location and experience. Trisura offers a comprehensive benefit package that includes medical, dental, and vision insurance, as well as 401(k) with company match and Employee Stock Purchase Plan.
www.trisura.com

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