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Insurance Sales Agent (Remote) - on target annual earnings: $100,000-$150,000+

August 3, 2026

About The Opportunity Come join one of the fastest-growing fintech startups in the U.S! At Jerry, we’re on a mission to help car owners save time and money on one of their most expensive and high maintenance assets. Since launching our mobile app in 2019, we have amassed over 5M customers, and expanded beyond insurance shopping to refinancing, safety and repairs to become the #1 rated AllCar app in the App Store. We are looking for a Remote Sales Representative who can work weekends and evenings to join our growing team! This role is 100% remote, we provide all work equipment needed. In this role, you will be responsible for helping prospective customers understand and choose the right insurance policies for them from one of Jerry's 55+ insurance carrier partners. All of our customers come to us directly from our mobile or web app, so no outbound calls needed. If you are looking for an opportunity to make a measurable difference in the lives of millions, we'd love to hear from you! Who You Are <ul><li>You can multitask and manage multiple competing priorities</li><li>You are passionate about helping others </li></ul>How You Will Make An Impact <ul><li>Respond to inbound calls from prospective customers for personal line auto and home insurance policies</li><li>Educate customers on insurance policy details such as coverage and pricing</li><li>Prepare and bind quotes through our carriers</li><li>Effectively problem solve and objection handle to remove barriers from the customer purchasing the policy with Jerry</li><li>Provide attentive, high energy conversation with customers that show we are actively engaged in finding a policy that best fits each individual's needs </li></ul>Compensation And Perks <ul><li>Hourly wage: $19.00 - 21.00 plus uncapped commissions (on target annual earnings: $100,000-$150,000+)</li><li>We will pay for your P&C license (expected within 2 weeks after starting)</li><li>Medical, dental, vision insurance, 401K match</li><li>Ability to work remotely (we provide work equipment)</li><li>Ongoing training and mentorship from our leadership team</li><li>An outstanding portfolio of insurance carriers and products - we work with over 55 carriers to ensure we can offer our customers the best options for them </li></ul>This role includes flexible scheduling options, with the choice between a 5-day, 8-hour schedule or a 4-day, 10-hour workweek. While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted. Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai Your car and your home are your most expensive assets. And for most people, these aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive. Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair or, worse, an accident, and help you sell at the best price when the time is right. That friend is Jerry. Jerry is building the first AI agent to manage all your physical assets. We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond. We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.

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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...