2

Remote Underwriter Trainee Jobs in Virginia (NOW HIRING)

While there is a preference to be based in Richmond, VA, we are open to a remote working location ... Underwrite healthcare liability insurance for long-term care facilities, social services agencies ...

While there is a preference to be based in Richmond, VA, we are open to a remote working location ... Underwrite healthcare liability insurance for long-term care facilities, social services agencies ...

Underwriter is responsible for underwriting residential mortgage loans to ensure compliance with bank, investor and secondary market standards. Communicates with processor, originators and other ...

Underwriter is responsible for underwriting residential mortgage loans to ensure compliance with bank, investor and secondary market standards. Communicates with processor, originators and other ...

Remote Underwriter Trainee information

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 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.

Can you work remotely as a remote underwriter trainee?

Remote underwriter trainees can often work remotely, depending on the employer and company policies. Many companies offer remote training programs and require proficiency with underwriting software and strong communication skills. Availability of remote work may vary based on the company's remote work policies and the specific role requirements.

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.

How to get a job as a remote underwriter trainee with no experience?

To become a remote underwriter trainee with no experience, focus on gaining relevant knowledge through online courses in insurance or finance, and develop skills in risk assessment and data analysis. Entry-level positions often require a high school diploma or equivalent, and demonstrating strong attention to detail and communication skills can improve your chances. Internships or volunteering opportunities can also provide practical exposure to underwriting processes.

What do remote underwriter trainees do?

Remote underwriter trainees assist in evaluating loan applications by analyzing financial documents, credit reports, and property information to determine risk and eligibility. They learn to use underwriting software and follow company guidelines under supervision, gaining skills necessary for full underwriting responsibilities.

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 cities in Virginia are hiring for Remote Underwriter Trainee jobs? Cities in Virginia with the most Remote Underwriter Trainee job openings:
Infographic showing various Remote Underwriter Trainee job openings in Virginia as of July 2026, with employment types broken down into 72% Full Time, 10% Part Time, 2% Temporary, and 16% Contract. Highlights an 43% Physical, 3% Hybrid, and 54% Remote job distribution.

Underwriter, Allied Medical

Hamilton

Richmond, VA • On-site, Remote

Full-time

Medical, Dental, Vision, Life, Retirement

Re-posted 16 days ago


Job description

We're looking for anUnderwriter, Allied Medical.

Working remotely or based in Richmond, Virginia and reporting to the Allied Medical Division Manager, who is based in Richmond,this role will help drive the development of the Allied Medical liability book. The purpose of this role is for a talented, dynamic, and technical Underwriter to bring healthcare liability underwriting experience to the Allied Medical team. This role will focus on Excess & Surplus lines placements using Hamilton Select's E&S platform that is rated A by AM Best.

While there is a preference to be based in Richmond, VA, we are open to a remote working location for appropriately qualified candidates.

The successful candidate will be responsible for developing and managing relationships with wholesale brokers in the US to build a profitable portfolio of Allied Medical liability insurance. Exceptional service is a must. This role will include occasional business travel.

What you will do

  • Underwrite healthcare liability insurance for long-term care facilities, social services agencies, drug and alcohol rehab organizations, group homes, adoption and foster care, home health care and medical staffing agencies, among others.
  • Contribute to Hamilton's strategy to grow and diversify the Healthcare portfolio.
  • Establish and maintain underwriting standards and discipline to ensure the delivery of profitable results
  • Underwrite business in accordance with guidelines to maintain underwriting standards and discipline to ensure delivery of profitable results.
  • Drive the general use of technology to produce superior profit and establish an ease-of-doing business reputation with our appointed trading partners
  • Originate, grow and develop high level market relationships with brokers.
  • Use critical thinking skills to negotiate terms.
  • Assist in training and mentoring of new employees.
  • Other duties as assigned.

What you require for the role

Key Attributes

  • An established underwriter with 3 plus years underwriting experience (handling healthcare and social services classes) and a strong technical reputation in the U.S. healthcare liability market, with the ability to further develop themselves.
  • Understands, is comfortable with, and able to support a business strategy that focuses on writing niche lines
  • Proven track record of generating new leads, applying sound judgement to a broad range of situations and opportunities, and building a substantial portfolio of business from a small base
  • Ability to attract business from existing relationships and to nurture and develop new relationships
  • Appreciation of both the subjective and objective aspects to underwriting risk and a willingness to justify decision-making processes at the highest levels in the organization
  • Breadth of understanding of market trends and nuances
  • Proven ability to generate an underwriting profit
  • Integrity in all internal and external relationships
  • Shared focus on expense management and managing the overall business operations to maximize shareholder returns

Other Personal Attributes:

  • Motivated, self-starter with an entrepreneurial mindset
  • Excellent verbal and written communication skills
  • Proven decision-making skills.
  • Good management, coaching and mentoring skills
  • Approachable and able to clearly market business
  • Keen attention to detail, highly analytical and excellent problem-solving capability
  • Demonstrates an understanding and capacity to effectively engage in the negotiation process. Dedicated and consistent

What you can expect from us

At Hamilton, we offer a vibrant, entrepreneurial and collaborative workplace shaped by our values: Be Smart, Be Sensible, Be Open and Be More.

Our employees consistently say they would recommend Hamilton as a great place to work - a testament to the inclusive, supportive, and empowering culture we've built together. We embrace individuality, value diverse perspectives, and recognize the unique contribution each person makes to our continued success.

Hamilton offers a competitive salary with an annual performance-based target bonus and a comprehensive benefits package, to include:

  • Hybrid working
  • Matching 401K plan
  • Medical, dental, vision, life, disability
  • Generous time off (including parental leave)
  • Continued support for professional development
  • Gym subsidy
  • My day (additional days leave for personal interests/wellness/charity work


In good company.

At Hamilton, we're building a global specialty insurance and reinsurance company focused on underwriting expertise, enhanced by data and technology to deliver significant shareholder value.

Headquartered in Bermuda, we operate on a global basis, with over 600 employees and key underwriting operations in London, Bermuda, the US and Dublin.

Join us as we continue to drive Hamilton's evolution into a diversified specialty insurance and reinsurance company. You'll be in an environment where our colleagues work collaboratively, share a passion for the service and results we deliver, and know that what we do each day is meaningful - to our customers and our business.