Licensed Healthcare Agent Trainee (WFH) - Pet Insurance & Pharmacy Support

Job Summary

Chewy is seeking a compassionate and detail-oriented Licensed Healthcare Agent Trainee to join our growing Pet Insurance & Pharmacy Support team. This work-from-home role is designed for individuals who are passionate about pet health, customer advocacy, and continuous learning. As a trainee, you will receive comprehensive training and support to become a licensed healthcare agent while delivering exceptional service to pet parents. You will act as a trusted resource, guiding customers through pet insurance inquiries, pharmacy-related questions, and policy support with empathy and accuracy.

Key Responsibilities

  • Provide professional, empathetic support to pet parents regarding pet insurance policies, claims, coverage details, and pharmacy services

  • Assist customers with prescription inquiries, refills, order status, and coordination with licensed veterinary pharmacies

  • Learn and comply with state licensing requirements and successfully complete required licensing exams within designated timelines

  • Accurately document customer interactions, claims information, and case notes using internal systems

  • Resolve customer concerns efficiently while maintaining compliance with healthcare, insurance, and data privacy regulations

  • Collaborate with internal teams including pharmacy operations, insurance specialists, and quality assurance

  • Maintain a high standard of service quality, productivity, and customer satisfaction metrics

Required Skills and Qualifications

  • High school diploma or equivalent required; associate or bachelors degree preferred

  • Strong verbal and written communication skills with a customer-first mindset

  • Ability to handle sensitive healthcare and insurance-related conversations with professionalism

  • Basic computer proficiency and ability to navigate multiple systems simultaneously

  • Willingness and ability to obtain and maintain required healthcare/insurance licensing

  • Reliable high-speed internet connection and a distraction-free home workspace

Experience

  • Previous experience in customer service, healthcare support, insurance, pharmacy, or call center environments is preferred

  • Entry-level candidates with strong communication skills and a willingness to learn are encouraged to apply

  • Experience working remotely or in a regulated environment is a plus

Working Hours

  • Full-time, work-from-home position

  • Flexible scheduling may include evenings, weekends, or holidays based on business needs

  • Paid training period with structured onboarding and coaching

Knowledge, Skills, and Abilities

  • Understanding of customer service best practices in healthcare or insurance settings

  • Ability to learn complex insurance plans, pharmacy workflows, and regulatory requirements

  • Strong attention to detail and organizational skills

  • Problem-solving ability with sound judgment and critical thinking

  • Emotional intelligence and patience when supporting pet parents during stressful situations

  • Ability to work independently while remaining engaged with a remote team

Benefits

  • Competitive hourly pay with paid training and licensing support

  • Comprehensive medical, dental, and vision insurance

  • Paid time off, holidays, and wellness programs

  • Employee discounts on Chewy products and services

  • 401(k) with company match

  • Career growth opportunities within Chewys healthcare, insurance, and operations teams

Why Join Chewy

At Chewy, our mission is to be the most trusted and convenient destination for pet parents everywhere. Joining Chewy means becoming part of a purpose-driven company that values empathy, innovation, and growth. You will work with passionate teammates, gain valuable healthcare and insurance experience, and play a meaningful role in improving the lives of pets and the people who love them—all from the comfort of your home.

How to Apply

Interested candidates should apply online through Chewys official careers page. Submit your updated resume and complete the application process. Qualified applicants will be contacted for the next steps, which may include virtual interviews and assessments. Chewy is an equal opportunity employer and welcomes applicants from all backgrounds.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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