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Outside Property Claim Representative Trainee Jobs

The Whiteside Agency

Outside Property Claim Manager

Largo, MD · On-site +1

$104K - $171K/yr

... Outside Property claim professionals. Provide guidance and direction to direct reports through a ... Serve as a field representative for the Home Office Property product, as requested. Reinforce LOB ...

The Whiteside Agency

Outside Property Claim Manager

Bowie, MD · On-site +1

$104K - $171K/yr

... Outside Property claim professionals. Provide guidance and direction to direct reports through a ... Serve as a field representative for the Home Office Property product, as requested. Reinforce LOB ...

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Outside Property Claim Representative Trainee information

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$78K

$165.5K

How much do outside property claim representative trainee jobs pay per year?

As of Jul 24, 2026, the average yearly pay for outside property claim representative trainee in the United States is $78,042.00, according to ZipRecruiter salary data. Most workers in this role earn between $52,500.00 and $90,000.00 per year, depending on experience, location, and employer.

What are some common challenges faced by an Outside Property Claim Representative Trainee, and how can they be overcome?

As an Outside Property Claim Representative Trainee, a common challenge is managing a diverse and unpredictable caseload, often requiring travel to different properties and interacting with policyholders who may be experiencing stressful situations. Developing strong organizational skills and effective communication techniques can help navigate these challenges. Additionally, learning to balance empathy with objectivity while investigating claims and collaborating with contractors, adjusters, and colleagues is crucial for success and professional growth in this role.

What does an Outside Property Claim Representative Trainee do?

An Outside Property Claim Representative Trainee is an entry-level professional who learns to investigate, evaluate, and settle property insurance claims that occur outside the office, such as homes or businesses. They receive training on inspecting damages, interviewing policyholders and witnesses, and documenting claim details. Their work involves traveling to claim sites, assessing property damage, determining coverage, and negotiating settlements under supervision. As trainees, they gain hands-on experience and develop skills required for full claim representative roles.

What are the key skills and qualifications needed to thrive as an Outside Property Claim Representative Trainee, and why are they important?

To thrive as an Outside Property Claim Representative Trainee, you need a solid understanding of property insurance principles, investigative skills, and often a bachelor's degree or equivalent experience. Familiarity with claims management systems, digital inspection tools, and sometimes state adjuster licensing is typically required. Excellent communication, negotiation, and time management skills help you effectively interact with policyholders and resolve claims efficiently. These competencies are crucial for accurately assessing property damage, ensuring fair settlements, and maintaining customer satisfaction.

What is the difference between Outside Property Claim Representative Trainee vs Outside Property Claim Adjuster?

AspectOutside Property Claim Representative TraineeOutside Property Claim Adjuster
CertificationsTypically required or preferred (e.g., state licensing)Often required or obtained during training
Work EnvironmentTraining phase, supervised fieldworkField inspections, claim assessments
Employer UsageTraining program within insurance companiesFull-time role handling claims independently
Search IntentEntry-level, training, career developmentClaim resolution, field work, decision-making

In summary, the Outside Property Claim Representative Trainee is an entry-level position focused on training and gaining experience, often requiring certifications and supervised work. The Outside Property Claim Adjuster is a fully responsible role where the individual independently assesses and settles claims in the field. Both roles are integral to the insurance industry but differ mainly in experience level and responsibilities.

More about Outside Property Claim Representative Trainee jobs
What cities are hiring for Outside Property Claim Representative Trainee jobs? Cities with the most Outside Property Claim Representative Trainee job openings:
What states have the most Outside Property Claim Representative Trainee jobs? States with the most job openings for Outside Property Claim Representative Trainee jobs include:
What job categories do people searching Outside Property Claim Representative Trainee jobs look for? The top searched job categories for Outside Property Claim Representative Trainee jobs are:
Outside Property Claim Representative Trainee jobs near you
Infographic showing various Outside Property Claim Representative Trainee job openings in the United States as of July 2026, with employment types broken down into 79% Full Time, 19% Part Time, 1% Temporary, and 1% Contract. Highlights an 87% Physical, 4% Hybrid, and 9% Remote job distribution, with an average salary of $78,042 per year, or $37.5 per hour.

Outside Property Claim Manager

The Whiteside Agency

Easton, MD • On-site, Remote

$104K - $171K/yr

Full-time

Medical, Life, Retirement, PTO

Posted 4 days ago

Job description

Who Are We?

Taking care of our customers, our communities and each other. That's the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Job Category
ClaimCompensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range$104,000.00 - $171,700.00
Target Openings
1
What Is the Opportunity?
This role is eligible for a sign on bonus.
LOCATION REQUIREMENT: This field position services Insureds/Agents in the Maryland area. The selected candidate must reside in the assigned territory. This position is based 100% remotely and may include a combination of mobile work and/or work from your primary residence.
*You will be issued a company vehicle for this position.*
Under general direction and as a member of the local line of business (LOB) management team, responsible for product quality and performance for a specific team of Outside Property claim professionals. Provide guidance and direction to direct reports through a continuous process of management involvement and frequent claim file review. Serve as a field representative for the Home Office Property product, as requested. Reinforce LOB Vision, Strategies, and Objectives through word and action. Select, lead, mentor, performance manage and develop staff.What Will You Do?
  • Attract, Retain and Develop World Class Talent:
  • Proactive recruitment of talent; work with management establishing and implementing a strategic staffing strategy.
  • Effective orientation and on-boarding.
  • Manage staff performance; implement strategies and plans to address staff development; identify and address training needs on an ongoing basis; provide frequent performance feedback.
  • Work with management to develop and implement effective training, performance development and succession planning.
  • Effective retention planning; proactively manage and respond to turnover.
  • Effectively utilize reward system to distinguish top performers and significant achievements.
  • Provide Compelling Claim Services:
  • Employ proper claim handling techniques to protect the integrity of our brand and providing consistent service quality and streamlined processes to add value for our customers.
  • Develop and execute a strategic file management plan that achieves optimal file resolution and business results.
  • Provide face-to-face and written guidance to ensure effectiveness, engagement, accuracy and efficiency.
  • Review new notices, ensuring claims are assigned to staff with appropriate skill sets.
  • Conduct quality file reviews per office/ best practices guidelines.
  • Conduct ride-along inspections/ reinspections with claim professionals to provide coaching and feedback.
  • Establish/follow up on file reviews per diary instructions, conducting additional reviews (i.e. 180, 360 day reviews), as necessary.
  • Implement strategies and initiatives to improve file quality, customer service and manage costs.
  • Drive the Information Advantage:
  • Successfully leverage data, management information and technology to identify and make the most of opportunities to support business strategies and improve results.
  • Achieve Optimal Solutions:
  • Focus on resolution and process improvement, fulfilling all obligations while maximizing cost effectiveness, helping the business understand drivers, trends and product stress points and helping our partners attract and retain business.
  • Operate within agreed upon expense budget to achieve optimal business results through productivity, appropriate resource allocation, inventory management and loss adjustment expense.
  • Partner for Mutual Success:
  • Develop and maintain effective relationships with colleagues, business partners, customers, agents, regulatory agencies and others to achieve organizational goals and create better outcomes.
  • Participate in business meetings and agency visits as required.
  • In order to perform the essential functions of this job, acquisition and maintenance of Insurance License(s) may be required to comply with state and Travelers requirements. Generally, license(s) must be obtained within three months of starting the job and obtain ongoing continuing education credits as mandated.
  • Access and inspect all areas of a dwelling or structure which is physically demanding requiring the ability to carry, set up and climb a ladder weighing approximately 38 to 49 pounds with a safety weight rating of up to 300 pounds (safety weight rating is the amount of weight the ladder can safely carry and includes weight of the individual and up to16 pounds of standard equipment), walk on roofs, and enter tight spaces (such as attic staircases and entries, crawl spaces, etc.).
  • Perform other duties as assigned.
What Will Our Ideal Candidate Have?
  • Bachelor's Degree.
  • Claim management experience.
  • Leading the Business:
  • Drive Results.
  • Leads Change.
  • Executes Business Strategy.
  • Leading Others:
  • Attract Top Talent.
  • Maximize Individual Performance.
  • Holds Others Accountable.
  • Aligns Rewards.
  • Creates and Sustains a Dynamic Workplace.
What is a Must Have?
  • High School Diploma or GED.
  • Three years claim work experience in at least one line of business.
  • Valid Driver's License.
What Is in It for You?
  • Health Insurance:Employees and their eligible family members - including spouses, domestic partners, and children - are eligible for coverage from the first day of employment.
  • Retirement:Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
  • Paid Time Off:Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
  • Wellness Program:The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
  • Volunteer Encouragement:We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.
Employment Practices

Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences.

In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.

If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.

Travelers reserves the right to fill this position at a level above or below the level included in this posting.

To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/.

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