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Insurance Jobs in Winchester, VA (NOW HIRING)

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Insurance information

See Winchester, VA salary details

$30.1K

$56.5K

$84K

How much do insurance jobs pay per year?

As of Aug 24, 2026, the average yearly pay for insurance in Winchester, VA is $56,547.00, according to ZipRecruiter salary data. Most workers in this role earn between $46,600.00 and $64,600.00 per year, depending on experience, location, and employer.

What do insurance agents do?

Insurance premium auditors are employees of a variety of companies. You can work with businesses who specialize in handling premium audits, risk management, or business process outsourcing, but most available positions are with insurance companies. You can choose a field based on the type of insurance you’re most familiar with such as workers’ compensation, car, home, or life insurance, or choose a company that works with all insurance types. Some positions require working on the phone, while others require traveling within an assigned geographic area.

What are the key skills and qualifications needed to thrive in an insurance professional role, and why are they important?

To thrive in an insurance role, you need strong analytical abilities, attention to detail, and a solid understanding of insurance products, often supported by a relevant degree or insurance-specific certifications such as CPCU or CLU. Familiarity with policy management software, customer relationship management (CRM) systems, and underwriting tools is commonly required. Excellent communication, problem-solving skills, and a customer-focused mindset help professionals build trust and effectively address client needs. These competencies are vital for ensuring accurate policy management, regulatory compliance, and delivering high-quality client service in a competitive industry.

What are some common challenges faced by professionals working in the insurance industry, and how can they be addressed?

Professionals in the insurance industry often encounter challenges such as staying updated with changing regulations, managing complex client needs, and handling a high volume of claims or policy inquiries. Navigating regulatory changes requires continuous professional development and attention to compliance updates. Effective communication and organizational skills are vital for managing client expectations and workloads efficiently. Building strong relationships with underwriters, claims adjusters, and clients can also help address these challenges and ensure successful outcomes.

What is the difference between Insurance vs Insurance Agent?

AspectInsuranceInsurance Agent
CredentialsVaries by role; may include licenses for specific insurance typesRequires state licensing and certification
Work EnvironmentOffice, online, or client sitesOffice, client meetings, or remote
Employer & IndustryInsurance companies, brokers, agenciesInsurance agencies, brokerages, companies
Job FocusDeveloping, selling, managing insurance policiesSelling insurance policies, client consultation

Insurance is a broad industry encompassing various roles, including Insurance Agents. Insurance Agents specifically focus on selling and advising clients on insurance policies, often requiring licensing. While Insurance professionals may work in different capacities, Insurance Agents are directly involved in client interactions and policy sales, making their roles closely linked but distinct within the industry.

What careers are there in insurance?

Careers in insurance include roles such as insurance agents, underwriters, claims adjusters, actuaries, and risk managers. These positions often require strong communication, analytical skills, and industry-specific certifications or licenses. The insurance industry offers opportunities in sales, customer service, underwriting, and claims processing within various companies and agencies.
More about Insurance jobs

What are the most commonly searched types of Insurance jobs in Winchester, VA?

The most popular types of Insurance jobs in Winchester, VA are:

What are popular job titles related to Insurance jobs in Winchester, VA?

For Insurance jobs in Winchester, VA, the most frequently searched job titles are:

What job categories do people searching Insurance jobs in Winchester, VA look for?

The top searched job categories for Insurance jobs in Winchester, VA are:

What cities near Winchester, VA are hiring for Insurance jobs?

Cities near Winchester, VA with the most Insurance job openings:

Insurance jobs near you
Infographic showing various Insurance job openings in Winchester, VA as of August 2026, with employment types broken down into 59% Full Time, 38% Part Time, and 3% Contract. Highlights an 95% In-person, 2% Hybrid, and 3% Remote job distribution, with an average salary of $56,547 per year, or $27.2 per hour.

Insurance Representative

Transamerica Life Insurance Company

Winchester, VA

$59K - $74K/yr

Full-time

Re-posted 7 days ago

Job description

The Insurance Representative is directly responsible for writing new quality business, conserving existing business, providing ongoing quality service to policy owners in accordance with the Insurance Representative’s Agreement and maintaining a program of continuous self-improvement. The primary aspect of the Insurance Representative position is to sell. All other functions, particularly policy owner services, provide the opportunities to increase sales activity.

The Representative reports directly to a Managing Representative, Associate Director or Managing Director and is expected to meet weekly and annual objectives agreed upon with his/her immediate supervisor for the number of submitted life & health applications, life and health placements, life & health annualized controllable increase, Personal Financial Planning (PFP) sales interviews, Quality Life Check-ups (QLCs), first year and renewal persistency, first year and renewal lapse limits and all other required annual objectives. The Representative, with his/her immediate supervisor’s approval, is responsible for the creation, development and implementation of action plans that are consistent with Company and personal objectives. In order to accomplish these goals, the Representative has to demonstrate the ability to work without close supervision and to work evening hours and weekends. The Representative is expected to perform at levels that will result in net premium growth on the agency to which he/she is assigned.

The Representative will establish annual individualized objectives on the Representative’s Marketing Plan. He/she will create, develop and implement the methods/activities/action plans necessary to achieve the annual objectives. The Representative will participate in an individual Action Planning Conference (APC) with his/her direct supervisor on a regular basis for the purpose of meeting the individual’s activity, sales, service and training goals established in the Representative’s Marketing Plan.

The Representative is expected to perform at levels that will result in net premium growth on the agency to which he/she is assigned.

Qualifications

Education – High school diploma required. An undergraduate college degree, in a business-related field (i.e., marketing, business administration, management, etc.) preferred.

Years and type of experience required/preferred – One to 3 years of experience in an insurance sales environment preferred, but not required.

Life and health insurance license is required.

Valid driver’s license and dependable/reliable transportation.

Establishes high goals and expectations. Able to start and persist with specific courses of action while exhibiting high motivation and a sense of urgency; willing to commit to long hours of work and make personal sacrifice in order to reach goals. Conducts oneself and communicates in a professional manner. 

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