Chief of Staff

Requirements

• 5+ years of work experience, at least 2 of them owning outcomes rather than tasks.
• Strong written English (C1+) and comfortable spoken English on a live call. You can write to an investor, a customer, and a vendor without sending the same email three times.
• You can turn a messy topic into a short document: situation, options, recommendation, next actions.
• You work comfortably in spreadsheets and can sanity-check costs and tradeoffs.
• You decide without full information, and you say so when you got it wrong.
• Discretion, because you will see everything, including what is not going well.
• Available 9am to 5pm US Pacific, Monday to Friday. I can flex the start to 8am if that suits your day better.
• Reliable internet with a backup plan, quality camera and headset, quiet workspace.
• Modern laptop with 24GB+ RAM.

This is probably not for you if

• You need tasks specified before you can start.
• You are looking for a strategy or advisory role.
• You would rather coordinate work than do it.
• You wait for approval on reversible decisions.
• You need your responsibilities to stay inside a defined box.
• You think AI output is finished work.

On AIWe are a slop-free startup.AI makes output cheap, it has not made reviewing that output any cheaper. Handing us unfiltered, unreviewed, verbose AI output moves your work onto someone else’s desk. That will get you fired.Use AI constantly, to take on more than one person could. Read everything before it leaves your hands.

Projects

Join a small San Francisco startup that builds creative tools on the cutting edge of AI. The team is remote and global.

The Role

You are the founder’s right hand.

Where an operations manager runs the systems that already exist, you take the first step on the ones that don’t.I want to hand you an outcome and then stop thinking about it.

• “Figure out whether we should launch this.”
• “Our onboarding is broken. Fix it.”
• “Find the right vendor, negotiate it, get implementation moving.”
• “We need a system for this. Come back with one.”

You work out what the actual problem is, research it, make the calls you can make, flag the ones I have to make, build the plan, and get the first chunk of it done before you bring it back to me.What I am hoping to hear back sounds like: “Here’s the plan. I posted the role, screened 40 applicants, and these are the five worth interviewing.”

What You'll Own

• Projects that do not belong to anyone yet, from framing through delivery.
• Hiring: sourcing, screening, scheduling, and keeping the pipeline honest.
• Contractors and artists, including scope, delivery dates, invoices, and follow-through.
• The operating cadence: what is tracked, what is overdue, what stopped moving without anyone noticing.
• Systems and SOPs for work that currently lives in my head.
• Investor outreach support: build the list, help send the emails, get the calls on the calendar.
• Whatever is on fire this month that nobody else can pick up.

Some of this is unglamorous. Calendar, inbox triage, and travel come with being the founder’s right hand. It is a small slice of the job, not the point of it, but if that part is beneath you then this is not your role.
What success looks like:

First 90 days. You have mapped what is in flight and what has stalled. I have stopped chasing status. You have taken at least two initiatives off me end to end.Ongoing. You bring me decisions with a recommendation attached rather than problems. Fewer things need me personally each month.

Benefits

Paid in USD, monthly. Fully remote. PTO: 12 days accrued at 1 day per month, increasing to 15 at year 1. Direct access to the founder, with no agency layer in between. GSuite, Notion, Slack, Attio, Monday.com, Loom, GitHub, and whatever AI tooling makes you fastest.

Backgrounds that tend to work

• Former founder, or agency owner and operator.
• Early employee at a startup where everyone did everything.
• Someone who has already been a founder’s right hand.
• Managed complicated client projects end to end.
• Built an operations function from nothing.

Your title matters much less to me than what you actually owned. If you have made payroll, chased an unpaid invoice, or sat across from an angry client, say so.