More than 80% of Americans own a car and see it as one of their biggest financial commitments, yet managing one still means paperwork, long phone holds, and app switching. Jerry.ai built the first app to manage it all: insurance shopping, refinancing, safety, and repairs—bringing an unexpected level of warmth and speed to an industry stuck in the past. Since launching in 2019, we’ve grown to over 5M customers.
Every customer comes to us looking for a better, easier way to handle their insurance. As an Insurance Sales Representative, your mission is to deliver an exceptional, consultative experience that turns initial interest into long-term customer trust, matching each individual with the ideal coverage from Jerry’s panel of 55+ carrier partners.
Who You Are:
A top performer: You have 2+ years of experience in sales, consultative account management, or high-touch service environments.
A customer champion: You bring genuine empathy, warmth, and active listening skills to every interaction, with a true passion for helping people.
A natural problem solver: You manage competing priorities effortlessly while maintaining a high standard of service and attention to detail.
How You'll Wow Our Customers:
Deliver standout customer experiences: Handle inbound calls for auto, home, motorcycle, and specialty insurance with high energy, patience, and genuine care.
Educate and advocate: Go beyond standard answers to uncover savings or coverage gaps customers didn't know to look for, translating complex policy details into clear, easy-to-understand choices.
Guide and bind: Craft tailored policy packages across our 55+ carrier partners and finalize coverage with ease.
Navigate friction thoughtfully: Listen to customer hesitation with empathy, addressing concerns directly to ensure a smooth, transparent purchasing experience.
Elevate the product: Act as the voice of the customer by sharing direct feedback with our product team to continuously refine our app and service offerings.
Compensation and Perks:
Hourly wage: $19.00 - $21.00 plus uncapped commissions (*Our most successful team members typically earn $100,000+ per year).
Fully funded licensing: We pay 100% of the cost for your P&C license (expected within 2 weeks after starting).
Benefits: Medical, dental, vision insurance, and 401(k) match.
Remote-first: Work from home with all equipment provided, supported by ongoing training and active team mentorship.
Flexible scheduling: 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 [email protected]
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.
Skills Required
- At least 2 years of experience in sales, consultative account management, or high-touch service environments
- Ability to obtain a property and casualty insurance license within two weeks after starting
- Current residence in an eligible state or Ontario, Canada, as applicable to the employment type
- Availability for a full-time schedule of either five 8-hour days or four 10-hour days
What We Do
At Jerry, we’re building a car ownership super app that puts comparison shopping, financing, driving, maintenance and parking solutions at your fingertips and savings in your wallet. We believe drivers deserve better. Why can’t shopping for insurance, financing and maintaining your vehicle be a click, a swipe or a text away? It should be. We’re making that happen. Our custom artificial intelligence, machine learning and bots allow us to provide the best, personalized service for all car ownership needs. The Jerry team’s focus on customer experience results in exceptional transaction speed. With our first product, Jerry redesigned and disrupted the century-old car insurance process, turning stacks of pages and hours of calls into a handful of clicks. That’s why we’re the only car insurance marketplace that gives you the best, customized quotes from more than 55 name-brand insurance carriers in 45 seconds. Jerry helps drivers shop for the best price, compare against current coverage, purchase without a single phone call (unless you want one!) and maintain the best policy for your needs. Led by serial entrepreneurs, tech elite alumni, and fintech, insurtech and auto experts, Jerry attracts people driven to create a customer experience that makes people happy by saving them money and time. And it’s working. Jerry is the #1 rated and most downloaded app in the category. With headquarters in the heart of Silicon Valley, offices in Toronto and Buffalo, and remote team members in four countries, Jerry has removed physical location from recruiting restraints to capture top talent. Join us. Awards: -One of only 50 U.S. startups to be named a LinkedIn Top Startup 2021. -Featured as one of 150 fastest-growing companies to accelerate your career by Otta in 2021. -Included in Forbes and Statista America’s Best Startup Employers 2022. -Ranked on Y-Combinator Top Companies List 2022. -Art Agrawal Named on of The Top 25 InsurTech CEOs 2022.
