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 re-sequenced the morning and sent the plan before they ask
A capital-firm partner is downstairs for a 7 AM with one of the founders, the caterer is running late, and a conference room isn't set. You've got the guest badged and seated, the food rerouted, and the room handled—before the meeting starts
We work out of iMessage, not a ticketing system. You don't wish for Jira. You decide how the group chats get organized and make iMessage work

You Might Be a Fit If…

You're an experienced EA, office manager, or admin who takes real pride in the craft—the kind of person energized by walking into a messy closet (or a chaotic office) and making it perfect, not embarrassed to be the one doing it
You've run an office or workplace before—vendors, guests, the physical space—and you treat it as your product, not a chore
You've supported a chaotic, high-velocity executive before—ideally in finance (hedge fund, PE, a trading desk), where the calendar never stops moving and the bond with your principal is tight
You make mistakes, learn from them once, and keep moving—no freezing, no spiraling, no going quiet when the pressure's on
You run toward problems. When something breaks, you fix it first and report after
You're a relentless prioritizer—a vendor flake, a candidate reschedule, a founder's flight, and a guest in the lobby all at once, and you know exactly what to do first
You adapt to the tools that exist instead of resisting them

Requirements

3+ years in executive support, office management, or administrative/workplace coordination—ideally a blend of all three
Proven ability to juggle calendars, travel, vendors, and a physical space at once without dropping balls
Exceptional responsiveness and organization—a real operating system for staying on top of everything, not just "I'm organized"
Responsive early, when the founders' day takes shape (5–6 AM)
Based in San Francisco, in-office at 425 Market Street. This is not a remote or hybrid role

Nice to Have

EA experience supporting ex-finance founders or principals (hedge funds, PE, trading)
Office management, workplace, or facilities experience—you've owned a space, not just supported one
Experience at an early-stage, hypergrowth startup
A track record people describe as "the person who just handled everything"

Not a Fit If…

You freeze when the volume spikes, or you go quiet and pull back when you're stressed
You need a clean job description with bullet points you can audit against—"that's not my job" is a phrase you reach for
You see administrative or workplace work as beneath you, or as a stepping stone to something "more strategic." Doing it brilliantly is the job
You need a mature org with ticketing systems and formal process to function. We run on iMessage and judgment
You hear feedback as criticism instead of coaching
You gravitate only to the fun, visible parts (events, decor) and let the operational backbone slip

Compensation

Salary: $130,000–$160,000 + performance bonuses & equity
Location: San Francisco, in-office at 425 Market Street

Schedule

Monday–Friday, in-office. The team rolls in between 5:15 and 5:45 AM, and the building runs hot until 7–9 PM. You don't need to stay that late—but you do need to be responsive and proactive early, when the day is being set. Start from home and come in a little later if that's how you work best; the early responsiveness is the non-negotiable, not the late stay.

Executive Assistant