Insurance Professional - Sales and Service (CHESAPEAKE)

USAA
Chesapeake, VA

Why USAA?

At USAA, our mission is to empower our members to achieve financial security through highly competitive products, exceptional service and trusted advice. We seek to be the #1 choice for the military community and their families.

Embrace a fulfilling career at USAA, where our core values – honesty, integrity, loyalty and service – define how we treat each other and our members. Be part of what truly makes us special and impactful.

The Opportunity

It is all about learning and growing. Our Insurance Customer Service role may be a new career for you. There’s a lot to learn, but the journey is mapped out and USAA is willing to invest in you! Our comprehensive, fully paid six-month training program includes all training materials, class discussions, hands-on training, e-learning modules, and the instructor led guidance will help you to support our membership independently. We also pay for all licensing costs!

Our in-office development program provides the training you need and the encouragement to create a proactive and independent support style to service our membership.

After six months in-office, you’ll have the opportunity to work offsite 2 days a week. The actual onsite days are settled between each employee and their manager.

We have various schedules ranging from 8:00 am CST to 10:00 pm EST with two days off. These roles include a shift differential of 15% for weekday hours worked after 6:00 pm local time and any hours worked on Saturday or Sunday.

Military veterans and spouses are highly encouraged to apply.

Relocation assistance is not available for this position.

As part of our licensing training program, you are required to obtain a property and casualty license for your state of residency by your third week of employment . We provide all study materials and pay for up to 3 licensing exam attempts. During your first 90 days, we will also provide you with resources to acquire additional state licenses to better serve our members.

We are currently seeking dedicated professionals to work in our Chesapeake office at 1341 Crossways Blvd, Chesapeake, VA 23320 for future insurance sales and customer service opportunities in June and July 2026 . As an Insurance Customer Service Representative, you'll work within defined guidelines to provide customer service, sales, and retention activities for multiple USAA Property & Casualty personal line products. You will assist members with new and existing USAA policies to deepen their relationship with the company. Representatives interact with our members across multiple contact channels to provide members adequate coverage and advice to help ensure their financial security.

What you'll do:

  • Facilitate the Property & Casualty member experience by handling inbound and outbound phone calls, emails, or other contacts from members.

  • Apply developing knowledge of personal lines' insurance to assist members with foundational to moderately complex quotes, binding new business, rating, policy, billing, payment, underwriting, contract and coverage provisions, and premium changes for insurance products and services. Also, maintain respective trailing documents for all states.

  • Identify, evaluate and understand member needs to consistently provide complete and accurate advice and solutions for insurance products and services. Provide detailed issue diagnosis while minimizing member transfers, escalations and call backs.

  • Efficiently operate in a contact center environment and navigate multiple systems and programs while maintaining an engaging member interaction that may occur across multiple channels.

  • Maintain required Property & Casualty license and state registrations.

  • Ensure risks associated with business activities are effectively identified, measured, monitored, and controlled in accordance with risk and compliance policies and procedures.

What you have:

  • High School Diploma or GED equivalent

  • Up to 1 year needs based sales and/or customer service experience in insurance, financial services and/or relevant direct customer service.

  • Acquire and maintain Property & Casualty (P&C) license and state registrations, within 90 days of hire. (Training, Licensing and State registration fees paid for by USAA.)

  • Demonstrated communication, problem-solving, and critical thinking skills to effectively respond to routine member inquiries.

  • Effective time management and organizational skills.

  • Successful completion of a job-related assessment may be required

What sets you apart:

  • 1 year of customer contact experience in a needs-based sales environment

  • 6 months experience frequently communicating (minimum 60 percent of the time) with customers by phone, e-mail, and/or face to face

  • US military experience through military service or a military spouse/domestic partner

Training Schedule: Monday - Friday

9:30AM-6:00PM Local Time

Work Schedule: Monday - Friday

9:00AM-5:30PM Local Time


USAA provides support to our members 7 days a week.

All work schedules for this role are 40 hours per week .
Work schedules are assigned based on business need and are subject to change to ensure adequate coverage for our members.

Compensation range: The hiring range for this position is: $45,010-$46,010

Compensation: USAA has an effective process for assessing market data and establishing ranges to ensure we remain competitive. You are paid within the salary range based on your experience and market data of the position. The actual salary for this role may vary by location.

Employees may be eligible for pay incentives based on overall corporate and individual performance and at the discretion of the USAA Board of Directors.

The above description reflects the details considered necessary to describe the principal functions of the job and should not be construed as a detailed description of all the work requirements that may be performed in the job.

Benefits: At USAA our employees enjoy best-in-class benefits to support their physical, financial, and emotional wellness. These benefits include comprehensive medical, dental and vision plans, 401(k), pension, life insurance, parental benefits, adoption assistance, paid time off program with paid holidays plus 16 paid volunteer hours, and various wellness programs. Additionally, our career path planning and continuing education assists employees with their professional goals.

For more details on our outstanding benefits, visit our benefits page on USAAjobs.com

Applications for this position are accepted on an ongoing basis, this posting will remain open until the position is filled. Thus, interested candidates are encouraged to apply the same day they view this posting.

USAA is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.

Posted 2026-05-04

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