Olli Insurance

Join The Solo Revolution

Help us build the insurance company that businesses of one actually want to work with. We're looking for people who get it – because they've been there.

Why Work At Olli?

We don't just insure solopreneurs - we embody their spirit, creating a workplace where autonomy meets purpose.

Mission That Matters

Every day you'll help solopreneurs protect their dreams. Our customers aren't just numbers – they're people building something from nothing, just like we are.

Human-First Culture

Flexible hours, unlimited PTO, and the understanding that life happens. We're building for the long term, not burning people out for short-term gains.

Move Fast, Build Better

Small team means big impact. Your ideas don't get lost in committees – they get built, tested, and shipped to thousands of customers.

Ownership & Growth

Equity for everyone, we are building something for continuous growth, and the chance to shape how an entire industry treats solo entrepreneurs.

Don't See Your Role?

We're always looking for talented people who share our mission. Send us your story.