Remote Insurance Agent, Sales or Service (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.

• 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).

• Stock 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.

• →

  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

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 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.