Remote Sales Associate - Retail/Service Backgrounds Welcome!

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Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.<br><br>We are looking for Remote Inbound Sales Agents who come from top-tier retail/service backgrounds like the Apple Store, Chick-Fil-A, Trader Joe’s or Costco. We are hyper-focused on <em>unreasonable</em> hospitality and are looking for ambitious individuals who are friendly, hard-working, and are incredibly service-oriented.<br><br><strong>This Role May Be a Fit For You If<br><br></strong><ul><li>You know that people don’t just come to a place for the product, they come for the experience. You know how to make a customer feel welcome, taken care of, and will go above and beyond to give them an incredible experience.</li><li>You’ve excelled in your retail job but are looking to transition into a long-term career with serious growth potential</li><li>You’re self-motivated and would enjoy a remote environment. This role can be done 100% remotely (goodbye, sore feet at the end of a long day!)</li><li>You thrive in a fast-paced & tech-focused environment: you’re used to handling several things at once while staying friendly. We’ll give you the best tools and tech to make that easy.<br><br></li></ul><strong>What You’ll Actually Do<br><br></strong><ul><li>Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)</li><li>Guide engaged users through the insurance purchasing process. There’s no cold-calling, these people have already started their insurance search in our app</li><li>Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.</li><li>Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.</li><li>Close the Deal: Help customers finalize their new policy right then and there.<br><br></li></ul><strong>What’s in it for you?<br><br></strong><ul><li>Pay: $19.00 - $21.00 per hour plus uncapped commission. *Our most successful team members typically earn $100,000+ per year.</li><li>We Pay for Your License: Don't have an insurance license? No problem. We pay for your training and your exam (usually completed in your first two weeks).</li><li>Work From Home: 100% remote. We provide all the equipment you need.</li><li>Flexible Schedule: Choose between working five 8-hour days or four 10-hour days.</li><li>Full Benefits: Medical, dental, vision insurance, and 401K matching.<br><br></li></ul><em>While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.<br><br></em><em><strong>Please note: </strong></em><em><strong>Jerry.ai</strong></em><em><strong> 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.<br><br></strong></em><em>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. <br><br></em><em>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 </em><em>recruiting@jerry.ai<br><br></em><em>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. <br><br></em><em>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.<br><br></em><strong>About Jerry.ai<br><br></strong>Jerry is building the first AI-powered advisor to manage all your physical assets.<br><br>Your car, home, and motorcycle 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.<br><br>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, and help you sell at the best price when the time is right. That friend is Jerry.<br><br>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 achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.<br><br>Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.<br><br>We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.<br><br>We are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, 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...