Freelance Customer Retention Jobs (NOW HIRING)

More than 80% of Americans own a car and see it as one of their biggest financial commitments, yet managing one still means paperwork, phone holds, and switching between apps that don't talk to each other. Jerry.ai built the first app to manage it all (insurance shopping, refinancing, safety, and repairs) and since launching in 2019, we've grown to over 5M customers.

Every one of those customers holds an active policy with one of Jerry's 55+ insurance carrier partners, and their needs don't stop the day they sign up: cars get added, drivers move out, lienholders change. As a Customer Service Agent, you're the person who takes that call, makes the change, and keeps the policy (and the customer) with Jerry.

How you will make an impact:

• Respond to inbound calls from existing customers
• Process service requests such as adding/removing vehicles and drivers, adding lienholder information, sending policy documents, etc.
• Help customers with questions they have regarding existing insurance policies in relation to coverages or policy benefits or make changes to existing policy
• Work to retain Jerry policyholders by actively finding solutions for customers who are at risk of cancellation

Who you are:

• You can multitask and manage multiple competing priorities
• You are passionate about helping others
• You have 2+ years of experience working in a call center environment

Compensation and perks:

• Hourly wage: $19.00 - 21.00
• We will pay for your P&C license (expected within 60 days after starting)
• Medical, dental, vision insurance, 401K match
• Ability to work remotely (we provide work equipment)
• Ongoing training and mentorship from our leadership team
• An outstanding portfolio of insurance carriers and products - we work with over 55 carriers to ensure we can offer our customers the best options for them

This role includes flexible scheduling options, with the 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.

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 recruiting@jerry.ai

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.