Chief of Staff to the CEO at WindBorne Systems

The role

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.

What you'll do

• 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

What I'm looking for

• 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.

Benefits

• 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.

Location

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