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Administrative Assistant/Customer Service Representative

Leonard Insurance Agency
Osterville, MA Part Time
POSTED ON 8/14/2026
AVAILABLE BEFORE 12/11/2026

Job Overview

Are you looking for a career, not just a job? Then you will want to work for a company that will help you grow and treats its employees and customers like family. We are seeking a dynamic and detail-oriented Administrative Assistant/Customer Service Representative to join our team!

Since 1906, Leonard Insurance has been a family owned and operated agency that understands a happy employee will lead to happy customers. We have a history of taking caring, motivated people and shaping them into insurance professionals. We are currently seeking a self-starter who is interested in a lucrative, recession-proof career helping people protect what means the most to them.

This vital role combines administrative excellence with exceptional customer support, ensuring smooth office operations and positive client interactions. The ideal candidate will be energetic, organized, and possess a passion for delivering outstanding service. In this role, you will assist clients with professionalism and enthusiasm. This paid position offers an exciting opportunity to develop your skills in a fast-paced environment while making a meaningful impact every day.

Requirements

  • An upbeat, positive, and enthusiastic attitude
  • Excellent phone etiquette
  • Willingness to help coworkers and be a team player
  • The desire to learn and grow
  • Superb customer service skills and problem-solving capabilities
  • Stellar organizational skills and the ability to multi-task in a fast-paced environment
  • Strong written and verbal communication capabilities
  • Demonstrated time management skills with the ability to prioritize tasks efficiently
  • Computer literacy including typing speed and familiarity with general office equipment
  • Solid understanding of computer programs like Outlook and Word
  • The ability to obtain a P&C license shortly after hiring
  • Previous experience in customer service roles preferred
  • Previous insurance industry experience is a plus but not required
  • High school diploma or equivalent required
  • One year customer service experience preferred
  • Salary is commensurate with experience

Responsibilities

  • Work closely with the Account Managers and assist with quotes, binders, and policy maintenance workflows
  • Frequently interact with customers to provide prompt and accurate service for claim submissions, billing questions and endorsements
  • Assist Account Managers in the maintenance of account files in accordance with company policies and compliance guidelines
  • Learn how to educate customers concerning their insurance options
  • Support office management activities such as filing, and organizing documents
  • Provide excellent customer service by responding promptly to inquiries via phone or email
  • Maintain confidentiality of sensitive information while handling administrative and client data
  • Ability to handle confidential information discreetly and professionally
  • Responsibilities for this position are designed to grow as you do
  • It is ok if you didn’t understand some of the responsibilities listed. You will have the opportunity to learn and grow in this position

Join us to be part of a vibrant team where your organizational talents and customer service skills will shine! This role offers an engaging environment where you can grow your career while supporting our mission of delivering exceptional customer service.

Pay: $15.00 - $25.00 per hour

Expected hours: 15.0 – 25.0 per week

Benefits:

  • Flexible schedule

Application Question(s):

  • Do you have a working knowledge and feel comfortable using Microsoft Outlook and Word?
  • Do you have the ability to type proficiently on a computer keyboard?
  • Do you enjoy interacting with customers and work with them to solve their problems?
  • Are you comfortable learning and using other computer programs?

Education:

  • High school or equivalent (Preferred)

Experience:

  • Customer Service: 1 year (Required)

Ability to Commute:

  • Osterville, MA 02655 (Preferred)

Work Location: In person

Salary : $15 - $25

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