Remote Inside Sales Associate (Insurance Tech Startup)

About Jerry.ai

Your car and your home are your most expensive assets. 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.

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.

About the Role

This role runs on two paths (sales and service). You don't have to know yet whether you're a sales person or a service person—we will figure this out together through the interview process. As a member of the Customer Operations team, you’ll help customers take care of their most important assets, their car and home, with warmth and speed they didn’t expect from an insurance company.

The work is fast-paced, high-energy, team-oriented, and fully remote. A few things our team members love about working at Jerry:

• Opportunities to shape the customer experience as the product and services are constantly evolving.
• Equity (stock options)—you own a piece of what you're building.
• A career path in one of the largest industries in the world—insurance.
• The colleagues you work alongside. Ask our team what they value most, and the answer is almost always the same: the people and the culture. Jerry is full of people who take their work seriously and take helping each other just as seriously.

Responsibilities

• Taking great care of our customers. Our team members don’t just answer the question asked—they catch the thing the customer didn’t know to ask about: a coverage gap, a discount they qualify for, or a renewal about to spike.
• Answering inbound calls from customers shopping for auto, home, motorcycle, and other policies, and from policyholders who need something changed.
• Getting deep on the product. With a large panel of insurance companies to work from, knowing which one fits which customer is the craft of this job. Our app evolves constantly, and knowing it inside out makes you the person customers trust to navigate it.
• Problem solving to remove barriers between a customer and the right coverage.
• Processing service requests—vehicles, drivers, lienholders, policy documents.
• Making the product better. Tell us what you're hearing. The feedback loop here is short enough that you'll see your suggestions ship.

Qualifications

• Prior work experience in customer service, sales, or hospitality is a plus, but not required.
• Genuinely friendly and positive attitude and willingness to work as a team.
• Strong work ethic.
• Strong problem-solving skills.
• Strong communication skills.

Pay

Sales: Hourly wage of $19.00 - 21.00 plus uncapped commissions. Our most successful team members typically earn $100,000+ per year.

Benefits

• Competitive wage and benefits (medical, dental, vision insurance).
• 401K match.
• Paid vacation time and paid parental leave.
• Equity (stock options).
• Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.
• Fully remote, with work equipment provided.
• We pay for your P&C insurance license if you don’t have one yet.
• Wellness benefits.

Schedule

• Fully remote.
• Flexible scheduling: a 5-day, 8-hour or a 4-day, 10-hour work week.

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.