Remote Sales Associate - Retail/Service Backgrounds Welcome!

Jerry is the #1 rated app for car owners, helping 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.

About the role

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 seek ambitious individuals who are friendly, hard-working, and incredibly service-oriented.

This role is ideal if you:

• Believe people come for the experience, not just the product, and excel at making customers feel welcome and taken care of.
• Have thrived in retail but want to transition into a long-term career with serious growth potential.
• Are self-motivated and prefer a 100% remote environment (no sore feet at the end of the day!).
• Thrive in a fast-paced, tech-focused setting, handling multiple tasks while staying friendly.

Responsibilities

• Complete (paid) training and obtain an insurance license (must pass the licensing exam to sell insurance).
• Guide engaged users through the insurance purchasing process—no cold-calling, as users have already started their search in our app.
• Simplify the process by helping customers compare 55+ insurance companies to find the best fit for their budget.
• Solve problems by listening to customer concerns and finding solutions that build confidence.
• Close deals by helping customers finalize their new policy on the spot.

Requirements

• Experience in top-tier retail or service roles (e.g., Apple Store, Chick-Fil-A, Trader Joe’s, Costco).
• Must reside in one of the following states: AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada.

Pay

$19.00 - $21.00 per hour plus uncapped commission. Top performers typically earn $100,000+ per year.

Benefits

• We pay for your insurance license training and exam (completed in your first two weeks).
• 100% remote work with all equipment provided.
• Flexible scheduling: choose between five 8-hour days or four 10-hour days.
• Full benefits: medical, dental, vision insurance, and 401K matching.

About Jerry.ai

Your car and home are among your most expensive assets, representing the life you’ve built. Yet managing them—buying, insuring, maintaining, repairing, selling—remains fragmented, complicated, and costly. Jerry is building the first AI agent to handle all your physical assets seamlessly.

We started with car insurance in 2019, became a top 3 broker in the U.S., and expanded into driving insights, diagnostics, and a repair marketplace. With 5M+ customers, $240M+ raised, and profitability since 2024, we’re now growing into home, motorcycle, RV, and beyond. We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.