Remote Inbound Sales Agent (Fintech)

Jerry.ai; Illinois; Remote; USD 54,443,000 - 60,174,000; Full time

Benefits offered by this job

Uncapped commissions

Licensing covered

Remote-first

Medical & dental benefits

Flexible schedules

Job summary

Jerry.ai is hiring Remote Inbound Sales Agents to assist signups through our app. You’ll provide consultative, high-touch service with empathy, educating customers about insurance options across 55+ carriers, and guiding them to complete a policy right over the phone.

We seek individuals from premier retail or customer-service backgrounds who can deliver warm, efficient interactions remotely. Expect uncapped commissions and full licensing support, plus comprehensive benefits and flexible

Qualifications

• Experience in a high-standard retail, hospitality, or service-driven environment.
• Excellent active listening and communication skills.
• Ability to explain complex topics clearly and simply.
• Comfort using internal tools and insurance platforms.

Responsibilities

• Welcome inbound shoppers and build trust over the phone.
• Explain policy details, discounts, and coverage across 55+ carriers.
• Address hesitations with empathy and guide customers to purchase.
• Help customers finalize their policy on the spot.

Skills

Customer service

Active listening

Empathy

Communication

Tech-savvy

Education

High school diploma or equivalent

Tools

CRM software

Insurance platforms

Internal tools

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 with an unexpected level of warmth, speed, and simplicity.

We’re hiring Remote Inbound Sales Agents from premier retail and customer-service backgrounds (Apple Store, Microsoft, Lululemon, Nordstrom, Disney, Costco) who know that world‑class experience is built on listening, educating, and making people feel cared for. You’ve mastered high-touch service on the sales floor; now bring those skills to a fully remote career with huge earning potential and professional growth.

Why Your Background Fits:

• Consultative, Not Transactional: Zero cold calling or high-pressure tactics. Customers come to us through our app asking for help, and you’re there to deliver peace of mind and tailored advice.
• Educate Like a Specialist: Just like guiding someone to the right tech gear or specialized fit, you’ll translate complex insurance details into clear, easy-to-understand choices.
• High-Energy Warmth: You know how to multitask in a fast-paced environment while keeping every customer interaction positive, personal, and effortless.

What You’ll Care for Our Customers:

• Welcome Inbound Shoppers: Connect with customers who started their search in our app, creating an immediate sense of trust and active engagement over the phone.
• Simplify the Complex: Uncover policy nuances, hidden discounts, and coverage gaps across 55+ carrier options so customers get the best possible protection for their budget.
• Solve with Empathy: Listen closely to hesitations, resolve concerns with patience, and make purchasing insurance feel refreshingly simple.
• Guide to Completion: Help customers finalize their ideal policy right on the spot, leaving them confident in their coverage.

What You Bring:

• The Service Standard: Experience in a high-standard retail, hospitality, or experience-driven environment (Apple, Lululemon, Nordstrom, Disney, etc.).
• Empathetic Communication: A genuinely upbeat attitude, strong active listening skills, and the ability to connect naturally with people.
• Tech-Savvy Multitasking: Comfort navigating internal tools and insurance platforms while maintaining a warm, fluid conversation.

Compensation & 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 cover 100% of your P&C licensing training and exam costs in your first two weeks.
• Remote-First: 100% work-from-home with all computer equipment provided.
• Full Benefits: Medical, dental, vision insurance, and 401(k) matching.
• Flexible Schedules: Choose 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

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.