Executive Assistant

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 hand to both founders. You own their calendars, their travel, and the thousand small things that make their days work—responsive before the day starts, anticipatory all the way through, the single person everyone trusts to know what’s happening and what happens next.

On the workplace side, you own the 425 Market office. The vendors who keep it running, the candidates and guests who walk through the door, the building logistics behind it all—that’s yours to run well, not just keep ticking over. When the office works, it’s because you made it work.

What You’ll Do

• Own the founders’ calendars and days — Their schedules, priorities, and the judgment calls about what moves and what doesn’t (who can talk to whom, which meetings are confidential, which candidate is top-tier). And when a perfectly built day detonates at 7 AM, you re-sequence it, route the right people to the right rooms, and protect the priorities—calmly
• Be the early signal — The day takes shape between 5 and 6 AM. You don’t have to be online 24/7, but you’re the person who has the day set and ready before it starts, and who adjusts on the fly when it changes
• Run travel and personal logistics — Doctor’s appointments, family coordination, airport and hotel arrangements for visiting family, the niece’s bachelorette the principal shouldn’t have to track. The personal and the professional, handled with the same care
• Run the office day-to-day — Own the 425 Market workplace end to end: keep it stocked, functional, and welcoming; manage the caterer and snack vendor; and own the third-party and vendor relationships that keep the place running
• Own the front door and guest experience — Greet candidates, guests, and capital-firm visitors in the lobby, handle building access and security registration, and submit building tickets so problems get fixed before anyone notices them
• Keep recruiting coordination moving — Reschedules, no-shows, interviewer feedback, candidate logistics. Keep a high-volume hiring machine moving without friction
• Keep the housing program from breaking — We house relocated employees in company units. You’re not running it full-time, but you keep an eye on transitions so a move-in or a lease never becomes an emergency

What this actually means at Harper (real examples):

• It’s 5:40 AM. A founder’s first three meetings just collided with a flight delay for visiting family. You’ve already …