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Underwriting Trainee Jobs in Silver Spring, MD (NOW HIRING)

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Underwriting Trainee information

See Silver Spring, MD salary details

$33.6K

$81.5K

$144.2K

How much do underwriting trainee jobs pay per year?

As of Aug 10, 2026, the average yearly pay for underwriting trainee in Silver Spring, MD is $81,543.00, according to ZipRecruiter salary data. Most workers in this role earn between $63,100.00 and $89,900.00 per year, depending on experience, location, and employer.

What do underwriting trainees do?

Underwriting trainees assist in evaluating insurance applications by reviewing applicant information, assessing risks, and determining coverage eligibility. They learn to analyze data, use underwriting software, and develop decision-making skills under supervision, often working in an office environment with ongoing training.

What is the difference between Underwriting Trainee vs Underwriter?

AspectUnderwriting TraineeUnderwriter
CredentialsTypically entry-level, may require a degree in finance, insurance, or related fieldProfessional certification often preferred, such as CPCU or similar
Work EnvironmentTraining programs, supervised tasks, learning-focusedDecision-making, risk assessment, independent or team-based
Job ResponsibilitiesAssisting in risk evaluation, learning underwriting processesEvaluating risks, approving or rejecting policies

In summary, an Underwriting Trainee is an entry-level role focused on learning and supporting underwriting tasks, while an Underwriter is a fully responsible professional making risk decisions independently.

How much do beginner underwriting trainees make?

Entry-level underwriting trainees typically earn between $40,000 and $55,000 annually, depending on the industry, location, and company size. Starting salaries may increase with relevant skills, certifications, and experience in risk assessment and insurance policies.

What is an underwriting trainee?

Underwriting Trainees are entry-level professionals who are learning how to evaluate insurance applications, assess risks, and determine appropriate coverage and premiums. They work under the supervision of experienced underwriters and receive training in company policies, industry regulations, and risk assessment techniques. The goal of an underwriting trainee is to develop the skills necessary to make sound decisions regarding accepting or rejecting insurance applications and to eventually become a fully qualified underwriter.

What kind of training and mentorship can an underwriting trainee expect during their first year?

As an Underwriting Trainee, you can expect a structured onboarding process that combines classroom learning with hands-on experience. Most insurance companies pair trainees with experienced underwriters or mentors who provide guidance on risk assessment, policy review, and client interactions. You’ll likely rotate through different insurance lines to gain a broad understanding of underwriting practices, and participate in team meetings to discuss real cases. This collaborative environment helps you build technical skills and professional networks, laying a solid foundation for advancement within the company.

How do you become an underwriting trainee?

To become an underwriting trainee, candidates typically need a bachelor's degree in finance, economics, or a related field. Relevant skills include analytical thinking and attention to detail, and some companies may require or prefer prior internship experience in insurance or finance. On-the-job training is provided, and strong communication skills are beneficial.

What are the key skills and qualifications needed to thrive as an underwriting trainee, and why are they important?

To thrive as an Underwriting Trainee, you need strong analytical skills, attention to detail, and a bachelor's degree in finance, business, or a related field. Familiarity with underwriting software, risk assessment tools, and proficiency in Microsoft Excel are typically required, and some employers may value progress toward professional certifications like CPCU. Effective communication, organization, and a willingness to learn help candidates stand out in this entry-level position. These skills and qualities are essential for accurately assessing risks, managing data, and building a successful foundation for a career in insurance underwriting.
What are the most commonly searched types of Underwriting jobs in Silver Spring, MD? The most popular types of Underwriting jobs in Silver Spring, MD are:
What are popular job titles related to Underwriting Trainee jobs in Silver Spring, MD? For Underwriting Trainee jobs in Silver Spring, MD, the most frequently searched job titles are:
What job categories do people searching Underwriting Trainee jobs in Silver Spring, MD look for? The top searched job categories for Underwriting Trainee jobs in Silver Spring, MD are:
What cities near Silver Spring, MD are hiring for Underwriting Trainee jobs? Cities near Silver Spring, MD with the most Underwriting Trainee job openings:
Underwriting Trainee jobs near you
Infographic showing various Underwriting Trainee job openings in Silver Spring, MD as of August 2026, with employment types broken down into 87% Full Time, 11% Part Time, and 2% Contract. Highlights an 68% Physical, 8% Hybrid, and 24% Remote job distribution, with an average salary of $81,543 per year, or $39.2 per hour.

Partner in Training

St. John Properties, Inc.

Windsor Mill, MD • On-site

$100K - $125K/yr

Full-time

Re-posted 26 days ago

Job description

Job Summary:

The purpose of the St. John Properties Partner in Training (PIT) Program is to prepare trainees to expand the company’s portfolio and become a regional partner. This is an intense 4-year program at the Baltimore headquarters. The PIT will learn every facet of the company’s full service and vertically integrated capabilities to include site selection, acquisition, development, design, construction, leasing, marketing and property management.

During the training period, the PIT will be competitively compensated and have a benefit package with other incentives. At the completion of the program and relocation to the WISCONSIN regional office, the PIT graduate will be competitively compensated and be eligible for equity participation in the future development.

Job Roles & Responsibilities:

Rotate through internal departments and successfully demonstrate understanding of the required skills for each respective department as detailed below:

During your rotation in Property Management, you will learn how to manage and operate stabilized assets, handle tenant payment disputes, negotiate contracts for maintenance vendors, and actualize the budget. You will also understand the expenses passed through common area maintenance charges and those handled directly by the landlord for development upkeep.

In Tenant Improvements, you will gain a strong understanding of how interior construction projects are bid out, awarded, and completed. You will send out construction drawings for prospective tenant buildouts to sub-contractors in a competitive bidding process, consolidate returned bids, and provide the Leasing team with the total construction cost.

Your rotation in Leasing will involve using your knowledge from Property Management and Tenant Improvements to negotiate the portions of a lease related to maintenance, operating expenses, real estate taxes, insurance, and landlord's construction obligation. You will also network with other brokers in the market, prospect for new tenants, and keep up with the marketability of the leasing portfolio.

In Acquisitions, you will work with the team to prepare, review, and negotiate purchase and sale agreements. You will also work on underwriting offering memorandums and help acquire new sites for the St. John Properties portfolio by working closely with the contracts and development teams.

During your rotation in Core and Shell Construction, you will bid out and manage construction projects for the company's ongoing pipeline of new buildings. You will gain exposure to the construction bid process, sub-contractors, and learn how to read, understand, and do take-offs from a set of construction drawings. You will also learn what is important to look for on-site to ensure the project is progressing under budget, in-line with the scope of work, and without major building errors.

Finally, in Development, you will shadow the SVP of Development and learn the steps required to successfully complete a development. You will gain exposure to rezoning properties, working with local and state agencies, and understanding the process to achieve building permits for construction. You will also learn what development looks for in potential acquisition sites and how to work cross-functionally with local officials, engineering teams, lawyers, and geo-technical teams.

Job Qualifications:

  • 3-5 years’ experience in commercial real estate management required
  • Master’s Degree in Real Estate or MBA with a real estate concentration preferred. Required to have completed prior to end of Partner In Training Program.
  • Proficiency in Microsoft Office Suite including Outlook, Word, Excel
  • Must possess strong verbal and written communication skills
  • Excellent organizational skills and continual attention to detail
  • Demonstrate ability to work independently as well as in a team environment
  • Ability to handle confidential information appropriately
  • Ability to establish priorities and meet deadlines

*Regular attendance onsite is an essential function of the job.