Chief of Staff to the CEO at WindBorne Systems (Redwood City, CA)Chief of Staff to the CEO

I'm John, CEO of WindBorne. I have more things I want to do than time to do them, so I need two functions covered: a chief of staff who is real operating leverage — taking meetings in my place, moving things forward without me, making calls on my behalf — and the EA work of calendar, travel, and the small well-defined tasks.

The complication is AI. It can do a lot of what an EA does, but not everything, and humans are still really valuable in a lot of ways. What I actually want is a combination: a human plus AI automations, where the human can close the feedback loop and build the automations themselves. The catch is that building those automations usually takes a software engineer, and a traditional EA usually won't know how.

I don't know what the right setup is yet — a person, software, or some mix. Part of this job is helping me figure that out, and you may have to do EA-like work until we do. Right now one of our software engineers is filling in as my chief of staff, and his engineering skills are too valuable elsewhere.

• Take meetings in my place with anyone: an investor, a big potential customer, someone senior in government, a CEO who wants to partner with us
• Fill the gaps and be a reliable EA for me when I need it
• Juggle a lot of miscellaneous work and keep it organized
• Own our most important decks. Build high-quality slides quickly yourself, and drive the ones you don't write — a board meeting where each executive owns a section, and someone has to chase every one of them to done and make sure the finished deck holds together
• Learn my point of view and the reasoning I'd apply, so you can make calls on my behalf
• Build actual automated systems with AI — not just prompt it — to take over more of the support function over time

• Learns new things fast and can show real understanding of complex subjects quickly
• Excellent at slide decks, and at project-managing a deck across people who don't report to you
• Scrappy, with strong follow-through and meticulous attention to detail
• Calm handling a lot at once, and genuinely organized
• Gets good work out of AI models. You don't need a software engineering background — this can be learned on the job — but you do need to find this changing landscape interesting
• Comfortable in a spreadsheet and in a team chat tool (we run on Zulip) Nice to have: startup or high-growth experience, engineering fluency, U.S. citizenship.

• 401(k)
• Dental insurance
• Health insurance
• Vision insurance
• Unlimited PTO
• Stock Option Plan
• Office food and beverages

Salary

• $130k–$180k. We consider a range of backgrounds and experience levels and adjust offers to be competitive with market rates.

1600 Bridge Pwky, Redwood City, CA. In person required.