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Artificial Intelligence, Software Development

Chief of Staff

San Francisco, California, United StatesOnsiteFull TimeChief / Executive$100,000–$200,000 /yrPosted 23 days agoHidden Gem · YC Startup

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Role summary

This role is for an early to mid-career Chief of Staff to support two founders in a fast-paced startup environment. The position involves a wide range of responsibilities, including managing fundraising data rooms, building financial models, improving CRM hygiene, running the hiring funnel, and assisting with sales motions. The ideal candidate is an expert in building and orchestrating agents, a strong writer, possesses excellent operating instincts, and is comfortable with ambiguity and travel. This role offers direct exposure to founders and key business decisions, with the opportunity to operate with significant autonomy.

**What you'll actually do**

The two founders are running founder-led sales US and international markets, recruiting, fundraising prep, product calls and customer escalations on the same day. You will own whatever needs owning that week. The work is real and the scope rotates.

A normal week might include running point on a Series A data room while the founders are in customer meetings, sitting in on a pipeline call and turning it into a follow-up sequence the next morning, building the financial model because the CFO function does not exist yet, drafting board updates and customer-facing one-pagers, cleaning up CRM hygiene because no one else will, running the hiring funnel for three open roles at once, flying to Orlando for a restoration trade show on 24 hours' notice, and telling a founder when something they want to do is the wrong call.

Most of this work is unglamorous. The job is to remove friction from the founders' calendar and to operate at a level where they trust you to make calls without checking in.

**Who you are**

You're early or mid-career and want a seat next to two founders building a company that matters. You're comfortable with ambiguity, you write well, are comfortable spinning claude and openclaw agents, you think in spreadsheets and you can hold ten threads at once without dropping any. You move fast and you finish things.

You want the reps that come from working inside a company where decisions get made in hours and shipped the same week.

Specific traits we care about:

* **Expert in building agents.** You can build agents and orchestrate multiple agents from scratch and pressure-test someone else's.
* **Strong writer.** You'll be drafting investor updates, customer emails and internal memos every week.
* **Operating instincts.** You spot what's broken and fix it before being asked.
* **Comfortable with a sales motion.** You can run discovery, follow up and keep deals moving even if you're not the closer.
* **Travel-tolerant.** The team operates across US and international markets

**What we offer**

Direct exposure to the two founders and every customer, investor and product decision. Cash compensation that's market for your geography, meaningful equity and a front-row seat to the Series A and what we build after.
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