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Chief of Staff

Lightspeed AI

The Opportunity

An early-stage company runs on founder hours, and founder hours are the scarcest resource we have. Every flight rebooked, every invoice chased, every context switch between a customer conversation and a vendor email is time taken from the product and the people we're building it for. Your mandate is to get that time back, measurably, and to make sure nothing important falls into the gaps between three busy founders.

This is not an executive assistant role, and it is not a shadow-executive role. It is an operator role with real ownership: you will take entire categories of work off the founders' plates and run them end to end, from processes and calendars to offices, events, and the internal tools that hold the company together. You will not simply keep the trains running; you will decide where the tracks go next.

The scope is designed to expand. What you take on in your first month is the foundation for what you'll own by the end of your first year, and because we're early, the version of this role that exists in two years is largely yours to invent.

What You'll Own

Founder leverage. You will run the systems that protect founder time and attention: travel booked and pre-scheduled before it's urgent, the standing cadence of investor check-ins, and a batched "this needs the CEO's signature" queue so decisions land once instead of leaking across the week. As you build context, you'll take on more of the surface area around the founders; balancing the design partner schedule and keeping its cadences honest, driving accountability through the recruiting pipeline, and pulling together the data points and proofreading behind investor updates.

Business operations. You will own the recurring machinery of the company: check-ins with our accountant and accountability to monthly and quarterly reporting deadlines, vendor management from scheduling through the back-and-forth of COIs and invoices, and AR/AP. You will be the on-site anchor for our Seattle office: the person the building, the contractors, and the punch list all route through, and over time you'll manage our offices across Seattle and the Bay Area, run office space searches, and own new employee onboarding so every hire's first week is a great one.

Special projects. This is the part of the role that grows the fastest. A weekly check-in on what's falling into the gaps and proactively raising what's about to. Representing the founders where they can't be. Dinners, office events, swag. Oversight of our advisors and mentors: are we meeting with them, are we getting value, where do we need new ones? And distinctly for this company: you will build internal tools with AI rather than buy or beg for them: go/ links, our hiring rubric, a comp planner, a competitive-intel bot, and you'll keep an operator's eye on our GTM and product metrics dashboards, incident response rates, and customer escalations, making sure everything looks sane and the right things get prioritized.

How We'll Know It's Working

We run this role on outcomes, not activity. In your first few quarters, success looks like: the founders each get 3->5 hours a week back and cut their context-switching in half; 5->10 projects and recurring activities move wholly off the founders' to-do lists and onto yours; and the company is running 30% more non-technical projects simultaneously because you made the room for them.

Who You Are

We would like to work with you if you are:

  • An owner, not a router: When something lands on your desk, it's handled. You close loops rather than forward them, and people stop checking on things they've handed you.
  • A proactive gap-finder: You notice what's about to fall through the cracks before it does, and you'd rather surface a problem early than be right about it later.
  • Trusted with the sensitive stuff: Signature queues, investor communications, compensation tools. This role sees everything, and you have the judgment and discretion to carry that.
  • A builder with AI: Faced with a recurring chore, your instinct is to build the tool that removes it. You don't need to be an engineer, but you should be excited to create working software with AI agents rather than maintain spreadsheets by hand.
  • Ruthless about priorities, warm about people: You can tell a vendor no, hold a recruiting pipeline accountable, and chase a deadline, and everyone still likes working with you.
  • Low ego, high conviction: You're comfortable doing the unglamorous work that makes a company run, and equally comfortable defending a well-reasoned call when it's challenged.
Working Environment

This role is based in Seattle and primarily on-site, being the physical presence in our Seattle office is part of the job, with occasional travel to our Bay Area hub.

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Vacancy posted 4 days ago
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