Remote Sales Agent (Insurtech Startup)

Jerry.ai • Part-time • Remote (Boston, Massachusetts, United States) • $100k / year • 4h ago

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 a Remote Sales Agent, 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 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 support remote work for most roles, 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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