Remote Sales Associate - Retail/Service Backgrounds Welcome!

Jerry; Arlington (VA); Remote; USD 52,000 - 110,000; Full time

Benefits offered by this job

Pay and commission

License paid

Remote work

Flexible schedule

Benefits

Job summary

Jerry.ai is seeking a Remote Inbound Sales Agent to guide engaged users through the insurance purchasing process, after training and licensing. You’ll work from home with 100% remote flexibility and a strong focus on hospitality, delivering an incredible customer experience across a fast‑paced, tech‑driven environment.

Earn $19–$21 per hour plus uncapped commissions; our top performers routinely exceed $100k annually.

Qualifications

• Experience in retail/service or guest-facing roles.
• Ability to thrive in a remote, fast-paced tech environment.
• Strong customer-centric approach and problem-solving skills.

Responsibilities

• Complete paid training and insurance licensing.
• Guide engaged users through the insurance purchasing process in the app.
• Help customers compare 55+ insurers to fit their budget.
• Listen to customer concerns and resolve issues confidently.
• Close the deal by finalizing the policy.

Skills

Customer service

Remote work

Communication

Job description

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.

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 unreasonable hospitality and are looking for ambitious individuals who are friendly, hard‑working, and are incredibly service‑oriented.

This Role May Be a Fit For You If

• 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.
• You’ve excelled in your retail job but are looking to transition into a long‑term career with serious growth potential
• 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!)
• 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.

What You’ll Actually Do

• Go through (paid) training and insurance licensing (note: you must pass your licensing exam to legally sell insurance)
• Guide engaged users through the insurance purchasing process. There’s no cold‑calling, these people have already started their insurance search in our app
• Simplify the Process: Help customers compare 55+ different insurance companies to find the one that fits their budget.
• Solve Problems: Listen to a customer’s concerns and find a solution that makes them feel confident in their choice.
• Close the Deal: Help customers finalize their new policy right then and there.

What’s in it for you?

• Pay: $19.00 - $21.00 per hour plus uncapped commission. *Our most successful team members typically earn $100,000+ per year.
• 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).
• Work From Home: 100% remote. We provide all the equipment you need.
• Flexible Schedule: Choose between working five 8-hour days or four 10-hour days.
• Full Benefits: Medical, dental, vision insurance, and 401K matching.

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 [e-mail]

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

Jerry is building the first AI‑powered advisor to manage all your physical assets.

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.

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.

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.

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.

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.

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.