The Problem 36 million businesses in America need insurance—it's not optional. 77% are underinsured. 40% have no coverage at all. The distribution system failed them: too slow, too opaque, too confusing. Over 90% of commercial insurance is still human-led. We're building the inverse: 90%+ AI-led, pushing toward the higher 90s. Not by patching legacy workflows—by building AI that makes humans more effective, improves the customer experience, and eliminates friction at every step. We're adding ~1,000 customers per month. We've grown 100x since last year. We're looking to do even more this year—and that's why we're hiring. The hardest entry-level job in tech—and the one that teaches you the most. The Thesis To build AI that actually works, someone has to understand the work at a molecular level first—every exception, every edge case, every decision that currently lives in someone's head. That someone is you. Every call you take becomes training data that makes our AI smarter. Every pattern you flag shapes the product. You're not adjacent to the AI—you're the reason it gets better. This is the real version of "getting into AI." Not watching from the sidelines. Doing the work that makes the system work. The Role Let's be direct: this is high-volume, high-intensity phone work. You'll talk with business owners all day—contractors, restaurant owners, consultants, trucking companies—capturing the information that powers everything downstream. Extended shifts. Back-to-back calls. It's a grind, and we won't pretend otherwise. Here's what makes it different: you're doing this at a YC-backed AI company that's grown 100x in a year. Your work directly feeds the AI systems we're building. You'll learn an entire industry from the inside. And there are real graduation paths—into product, sales, account management, or engineering—for people who prove they can execute.
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Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed