Deputy Chief of Staff

Job Description Deputy Chief of Staff at Firecrawl. You will be the person who makes sure everything runs smoothly and increasingly become the go‑to person when critical actions are needed. Your day-to-day will revolve around recruiting, HR, onboarding, events, executive support, vendor and financial operations, and the systems that integrate all of it. About Firecrawl Firecrawl is the easiest way to turn the web into data that AI agents can use. One API call converts any URL into clean, LLM‑ready markdown or structured data – solving the hard problem that every LLM‑based product faces. We hit 8‑figures in ARR in year one and more than doubled it in year two, with 147k+ GitHub stars and developers, agents, and AI companies building on us every day. What You’ll Do Own whole pieces of People & Operations end to end – recruiting coordination, onboarding, HR operations, events, vendor and expense management Be the trusted second who can step in on almost anything when it needs to happen Build and run the systems that keep a fast‑growing team organized and improve them continuously Support the executive team through preparation, coordination, follow‑through, and quietly ensuring nothing falls through the cracks Tackle ambiguous, unowned problems without a specification and get them done Grow into more scope over time as you earn trust What We’re Looking For You are a high‑ownership generalist who has run operations or been the “person who makes things happen” at a fast‑growing company You have exceptional judgment and follow‑through; when you say something’s handled, it is handled You are comfortable with ambiguity and wide scope and would rather own a problem than wait for direction You can hold a hundred threads and remain calm enough that no one can tell You are discreet and trustworthy, handling sensitive people, compensation, and company matters close to the executive team You move fast and close the loop – you’d rather ship, adjust, and iterate than wait for perfection What We’re NOT Looking For Someone who needs a clearly defined lane and a full spec before they can act A pure coordinator who executes tasks but won’t own outcomes A person who wants a predictable, narrow role – this job is the opposite 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 Salary that makes sense — $150,000–$185,000/year, based on impact, not tenure Earn competitive equity as part of the team Generous PTO — 15 days mandatory, any additional days after 24 are on a first‑come, first‑served basis (holidays excluded); take the time you need to recharge Parental leave — 12 weeks fully paid for all parents Wellness stipend — $100/month for gym, therapy, massages, or whatever keeps you healthy Learning & Development — expense up to $1,000/year toward professional growth Team offsites — a change of scenery, minus the trust falls Sabbatical — 3 paid months off after 4 years Medical, dental, and vision coverage at 100% for employees and 50% for spouses/kids Life & disability insurance, including short‑term, long‑term, and optional supplemental plans Telehealth – consult a doctor from your couch 401(k) plan – start saving for retirement early; we’ll match Pre‑tax benefits – Access to FSAs and commuter benefits (US‑only) Pet insurance – because fur babies are family too Office perks for SF‑based employees – snacks, drinks, team lunches, ping‑pong, and startup energy E‑Bike transportation – a loaner electric bike to get around the city for free Interview Process Application Review – Submit work samples and a brief note explaining why you’re excited. We focus on what you’ve done, not where you studied. Intro Chat (~25 min) – A quick conversation to get to know each other and discuss your experience and what you’re looking for. You’ll have time for questions. Working Session (~45 min) – Run through a real operational scenario from our world, prioritise it, and deliver results. We evaluate your thinking and ownership. Founder Chat (~25 min) – Discuss culture, pace, ownership, and your preferred working style. You’ll also ask questions. Paid Work Trial (1‑2 weeks) – Take on a scoped operational piece with the team, paid at a contractor rate. It’s the truest signal for both sides. Decision – We move fast after the trial. If you want to be the person a fast‑moving company can’t run without and grow with, we’ll invite you to join. Apply now. #J-18808-Ljbffr