Executive Assistant to the CEO

You'll be the person who makes sure nothing falls through the cracks in our CEO's world — his calendar, his inbox, his commitments, his time. This is a role built on trust, precision, and quiet excellence. You won't be asked to reinvent the wheel. You'll be asked to make sure every wheel turns exactly when it should, every single day. You'll report directly to the CEO.

Salary Range: $150,000–$180,000/year (Range shown is for U.S.-based employees in San Francisco, CA.)

Equity Range: Up to 0.05%

Location: San Francisco, CA (In-person)

Job Type: Full-Time

Experience: 3+ years as an Executive Assistant, or equivalent operational support experience

Visa: US Citizenship/Visa required

About Firecrawl

Firecrawl is the easiest way to extract data from the web. Developers use us to reliably convert URLs into LLM-ready markdown or structured data with a single API call. In just over a year, we've hit 8 figures in ARR and 100k+ GitHub stars by building the fastest way for developers to get LLM-ready data.

We're a small, fast-moving, technical team building essential infrastructure super-intelligence will use to gather data on the web. We ship fast and deep.

What You'll Do

Own the CEO's calendar with zero ambiguity. Every meeting has a purpose, an agenda, the right attendees, and the right prep attached — or it doesn't get scheduled. You'll manage competing requests, protect deep work time, and make judgment calls about what deserves the CEO's attention and what doesn't. The calendar is your system, and it runs flawlessly.

Triage the inbox so nothing gets lost. The CEO's inbox is high-volume and high-stakes. You'll build and maintain a triage system that surfaces what's urgent, drafts responses where appropriate, and ensures that important threads — investor follow-ups, customer escalations, partnership opportunities — never stall because they got buried. Inbox zero isn't aspirational; it's the standard.

Ensure every commitment has follow-through. Prepare briefing materials and context docs before key meetings. Capture action items afterward and track them to completion. Coordinate logistics for board meetings, investor updates, and external engagements with the kind of attention to detail that makes people wonder how everything always runs so smoothly.

Handle sensitive information with complete discretion. You'll have access to confidential conversations, financials, personnel decisions, and strategic plans. Discretion isn't a nice-to-have — it's the foundation of this role. You protect the CEO's trust and the company's confidence by never letting sensitive information travel where it shouldn't.

Take care of the operational details. Travel arrangements, expense reports, scheduling logistics, and the hundred small things that keep an executive's work life running. You don't see these as beneath you — you see them as the backbone of everything else working.

Use AI tools to make your systems even tighter. We're an AI company, and we expect you to use AI tools — Claude, ChatGPT, automation platforms — to streamline your own workflows. If there's a repetitive task, your instinct should be to systematize it. You don't need to be an engineer, but you should be the kind of person who's already experimented with these tools.

Earn deeper context over time. This role starts tactical — owning the calendar, inbox, and logistics — and expands as trust is built. Over time, you'll gain visibility into strategic priorities, leadership dynamics, and company planning. The more you prove your judgment and discretion, the more context and responsibility you'll earn.

What We're Looking For

Borderline obsessive about details and follow-through. You're the person who triple-checks the meeting link, confirms the dinner reservation, and flags the scheduling conflict before anyone else notices. Nothing slips. That's not a goal for you — it's how you're wired.

High emotional intelligence and low ego. You read rooms well. You know when the CEO is overloaded before he says it. You navigate sensitive dynamics — board members, investors, candidates, team members — with grace and good judgment. You don't need the spotlight; you need things to run right.

Trustworthy at the highest level. You've held confidential information before and it stayed confidential. Period. You understand that discretion isn't just about keeping secrets — it's about knowing what to share, with whom, and when.

Executes to spec, fast, and doesn't freelance on priorities. When the CEO says "handle X by Thursday," it's handled by Wednesday. You don't reinterpret the ask or go rogue on priorities. You clarify when needed, execute precisely, and close the loop.

Slightly overqualified and happy about it. You might have the skills to do a bigger role, but you genuinely love the craft of executive support. You find deep satisfaction in building systems that make someone else dramatically more effective. You're not looking for a stepping stone — you're looking for the right person to support.

Comfortable with technology. You don't need to code, but you should be fluent in modern productivity tools — Google Workspace, Slack, Notion, calendar management tools — and genuinely curious about AI tools that can make your work better.

Backgrounds that tend to do well: EAs who supported a founder or CEO through a high-growth phase and became the person that executive couldn't function without. People with a track record of community leadership, service-oriented work, or roles where reliability and conscientiousness were the whole job. Anyone whose references would describe them as "the most organized and trustworthy person I've ever worked with."

What We're NOT Looking For

A strategist looking for a seat at the table. This role earns strategic context over time, but the starting point is execution, not vision. If you're looking for a role where you shape company direction from day one, this isn't it.

Someone who just books meetings. If your approach to calendar management is "put it on the calendar when someone asks," this isn't the right fit. We need someone who builds and maintains a system — not someone who waits to be told what to schedule.

Someone looking for a strict 9-to-5. This role pays well because the CEO's world doesn't stop at 5pm. There will be moments — a last-minute board prep, a travel change, an urgent request — that need you outside regular hours. It's not every day, but when it happens, you're on it.

A Note On This Role

The best executive assistants we've talked to describe their work the same way: "I make sure nothing breaks." That's exactly what we're looking for. Not someone chasing adrenaline or big-picture strategy — someone who finds deep satisfaction in building bulletproof systems around an executive and executing them with precision, warmth, and total reliability. If that sounds like you, we want to talk.

A Note On Pace

We operate at an absurd level of urgency because the window for what we're building won't stay open forever. If that excites you, keep reading. If it doesn't, no hard feelings — but this role probably isn't for you.

Benefits & Perks

Available to all employees

• Salary that makes sense — $150,000–$180,000/year, based on impact, not tenure

• Own a piece — Equity in what you're helping build

• Generous PTO — 15 days mandatory, anything after 24 days, just ask (holidays excluded); take the time you need to recharge

• Parental leave — 12 weeks fully paid, for moms and dads

• Wellness stipend — $100/month for the gym, therapy, massages, or whatever keeps you human

• Learning & Development — Expense up to $1,000/year toward anything that helps you grow professionally

• Team offsites — A change of scenery, minus the trust falls

• Sabbatical — 3 paid months off after 4 years, do something fun and new

Available to US-based full-time employees

• Full coverage, no red tape — Medical, dental, and vision (100% for employees, 50% for spouse/kids) — no weird loopholes, just care that works

• Life & Disability insurance — Employer-paid short-term disability, long-term disability, and life insurance — coverage for life's curveballs

• Supplemental options — Optional accident, critical illness, hospital indemnity, and voluntary life insurance for extra peace of mind

• Doctegrity telehealth — Talk to a doctor from your couch

• 401(k) plan — Retirement might be a ways off, but future-you will thank you

• Pre-tax benefits — Access to FSAs and commuter benefits (US-only) to help your wallet out a bit

• Pet insurance — Because fur babies are family too

Available to SF-based employees

• SF HQ perks — Snacks, drinks, team lunches, intense ping pong, and peak startup energy

• E-Bike transportation — A loaner electric bike to get you around the city, on us

Interview Process

Application Review — Send us your resume and a quick note on why this role excites you. Bonus points if you tell us about a system you built that made an executive's life dramatically easier.

Operational & Fit Interview (~45 min) — We'll dig into how you've managed executive priorities in the past, how you handle competing demands, and how you think about protecting time. We'll walk through a real scenario — a messy week of scheduling conflicts, urgent requests, and competing priorities — and see how you'd navigate it.

Founder Chat (~30 min) — Culture, pace, working style, and how you like to operate. This is with Caleb. Time for your questions too.

Paid Work Trial (1 week) — The real thing: step into the role for a week and show us how you'd run it. We'll evaluate on judgment, initiative, and how much smoother things feel with you in the seat.

Decision — We move fast after the trial.

If you're the kind of person who sees a disorganized inbox and physically can't leave it alone — and you want to be the force multiplier behind the CEO of one of the fastest-growing AI infrastructure startups — this is your shot.

Apply now and let's make every hour count.

Compensation Range: $150K - $180K