Deputy Chief of Staff

About The Opportunity Jul 23, 2026 San Francisco Bay Area, United States Deputy Chief of Staff About The Opportunity This is a rare seat at an AI company that's actually working. Prentis AI (formerly Hive Labs) builds computer-use models – AI that operates real software the way people do – and puts them to work inside some of the largest companies in retail, healthcare, and manufacturing. The team is small, the customers are large, and the work is the hard last-mile problem that decides whether enterprise AI is real. You'd sit at the center of it, working alongside the Chief of Staff and directly with the Founder, with real ownership and the room to make decisions that matter. It's the fastest education there is in how a company gets built – legal, press, customers, hiring, and everything in between that never fits neatly on an org chart. If you'd rather own outcomes than wait for a task list, this is the job. Founded by repeat builders behind LinkedIn, Zynga, and multiple exits, with a research team from OpenAI, Google DeepMind, and Meta. About The Role We're looking for a Deputy Chief of Staff who can operate as a genuine second-in-command to our Chief of Staff, not a support layer beneath one. In practice that means you take real ownership of workstreams, make decisions inside a clear mandate, and stand in for the Chief of Staff when needed – including in front of the Founder and outside parties. The work is broad and rarely the same two weeks running. On a given week you might review a contract, manage a press question, prepare a regulatory briefing, and run point on a hire. What stays constant is the level of trust and judgment required, and the expectation that you close things out rather than hand them back. We care more about how you think and what you've owned than about years on a résumé. Three to five years of relevant experience is the right range, but the bar is judgment, not tenure. What you’ll do Own significant projects end to end – deals, hires, launches, and escalations – with the authority to make the call the Chief of Staff or Founder would make. Step in for the Chief of Staff when they're stretched or unavailable: run the meeting, hold the decision, and represent the Founder. Handle first-pass review of contracts and agreements, flag the real risks, manage the back-and-forth, and coordinate outside counsel so only genuine decisions reach the Founder. Draft external communications, help manage press and reputational matters, and prepare the Founder for interviews and public appearances. Track policy and regulatory developments relevant to the company, and manage relationships with advisors, lobbyists, and officials. Take on the urgent, undefined problems that would otherwise pile up — unblock people, chase down loose ends, and resolve things quietly. Serve, alongside the Chief of Staff, as a trusted point of contact between the Founder and his personal and professional network, handling sensitive matters with discretion. What we're looking for 3–5 years in operations, strategy, legal, consulting, banking, or a comparable role. A mix of backgrounds is a plus. Strong writer and communicator, comfortable moving between a contract redline and a press statement in the same day. Good judgment under ambiguity, and the confidence to make decisions and own the results. The presence to represent the Founder and the company credibly with senior outside parties. Discretion above all. This role sits close to sensitive legal, financial, personnel, and personal matters, and confidentiality is central to it. Highly proactive, with a track record of taking ownership without being asked. Comfortable using AI tools to work faster and cover more ground. #J-18808-Ljbffr