Remote Inside Sales Associate (Insurance Tech Startup)

This job is what Jerry is all about: helping our customers take care of their most important assets, their car and home, with the kind of warmth and speed they didn't expect from an insurance company.
Car and home are people’s most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to help people manage it all.

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.

• Competitive wage and benefits (medical, dental, vision insurance, 401K match, paid vacation time).

• Equity (stock options) — we're a tech startup, and you own a piece of what you're building.

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

• Fully remote, with work equipment provided.

• A career path in one of the largest industries in the world — insurance. We pay for your P&C insurance license if you don’t have one yet.

• And, importantly, 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.

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 in the Customer Operations team, some of your responsibilities could include:

• 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. A renewal about to spike.

• Answering inbound calls from customers shopping 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 too, 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.

Who you are:

• 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

Compensation and perks:

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

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 have been profitable since 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 are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.