ExecutiveAssistant

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 person who keeps the founders, the office, and the day from falling apart. The calm at 5 AM when everything is moving at once. THE THESIS Harper is founder-led and operationally intense. The founders are in the details—submissions, strategy, hiring, partnerships—from 5 AM on. That intensity is how we grew 100x in a year. But every hour the founders spend rescheduling a doctor's appointment, chasing a flight for visiting family, fielding a vendor, or rebuilding a calendar that just blew up is an hour they're not building the company. This role exists to win those hours back. That's the bet: the right person in this seat doesn't just absorb the logistics—they give the founders back the one thing they can't make more of, and the company moves faster because of it. This is a demanding seat—the pace is real, the volume is high, and the day can change by the hour. The person who thrives here isn't rattled by that; they're energized by it. They run toward the problem, make the call, and take quiet pride in being the one who keeps it all together. THE ROLE This is a blended seat. Half of it is executive support to two founders; half of it is running the workplace they operate out of. The administrative and operational work is the job—done brilliantly—not a stepping stone to something "more strategic." On the executive side, you're the operational right h