Executive Assistant to the CEO

Executive Assistant to the CEO

You'll be the operational engine behind our CEO's day — owning his calendar, inbox, and priorities so he can focus on building the company. This is a high-agency role for someone who thrives on creating order, protecting executive time, and using every tool available (especially AI) to make things run faster and smoother. 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 like it's a product. Scheduling, rescheduling, ruthlessly protecting focus time. You'll prioritize meeting requests based on company goals and the CEO's current priorities — and say no when needed. Every meeting on the calendar has a clear purpose, agenda, relevant docs, and the right attendees, or it doesn't happen.

Triage the inbox to zero. Manage and prioritize the CEO's email — flag what's urgent, draft responses, archive noise, and make sure nothing critical falls through the cracks. You'll build systems to categorize and route communications across email, Slack, and other channels so the CEO only touches what actually needs him.

Make every meeting count. Prepare briefing materials, talking points, and context docs ahead of key meetings. Capture action items and track follow-through. Coordinate logistics for board meetings, investor updates, and external engagements.

Handle the administrative backbone. Travel arrangements, expense reports, and the operational details that keep things running. Manage confidential information with discretion and good judgment.

Use AI to make everything faster. Proactively use AI tools — Claude, ChatGPT, automation platforms — to streamline workflows. We're an AI company and expect you to leverage these tools daily. If something is repetitive, your instinct should be to automate it, not endure it. Stay current on new productivity tools and bring ideas to improve how the CEO and leadership team operate.

Work directly with the CEO. This role reports to Caleb. You'll have full context on his priorities and the autonomy to make judgment calls about his time.

What We're Looking For

An organizer who creates order out of chaos. You don't just manage a calendar — you build systems that make the entire executive workflow run better. You anticipate needs before they're expressed and think two steps ahead.

A sharp communicator who can speak for the CEO. You can draft emails, messages, and documents that sound like the person you support. You know when to be direct, when to be diplomatic, and when to just handle it yourself.

Someone with high judgment and discretion. You know what to escalate, what to handle independently, and what can wait. You've earned trust from executives before and you understand why that trust matters.

Genuinely excited about AI tools. You don't just tolerate technology — you seek out new tools and find ways to make them useful. You've already experimented with AI assistants, automation platforms, or workflow tools in your current role.

Proactive, not reactive. If you wait to be told what to do, you'll stall here. The best EA for this role sees a gap and fills it before anyone asks.

Backgrounds that tend to do well: EAs who've supported startup founders or CEOs through hypergrowth. Operations-minded people who ended up running an executive's entire work life. Anyone who's been told they're "terrifyingly organized."

What We're NOT Looking For

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 actively shapes how the CEO spends time.

People who avoid technology. If learning a new tool feels like a chore, you'll be frustrated here. We move fast and adopt new tools constantly.

Anyone who needs heavy direction. There's no playbook for this role. You'll build the playbook. If you need someone to define every task before you can start, this won't work.

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 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.