Executive Assistant to Founder

Executive Assistant to Founder Report to: Founder Hybrid: San Francisco - 3-5 days week in office Full Time - PT timezone Occasional, optional travel for events (NYC/London/Tokyo/Singapore) Overview Shawn “swyx” Wang is one of the best-known voices in AI engineering — writer, host of the Latent Space podcast, and founder of AI.Engineer and Smol.AI. This role exists to give him time back: a dedicated Executive Assistant who owns his calendar, inbox, travel, and day-to-day logistics completely enough that he can stay focused on writing, building, and speaking. This is a hands‑on, high‑trust support role — not a strategy, operations, or chief‑of‑staff position. AI.Engineer’s business operations are owned by our Head of Ops, who this person will work alongside. This role is scoped to Shawn himself: his time, his commitments, his context. You won’t be setting direction; you’ll be the reason he doesn’t have to. What This Role Actually Requires This is not a task‑execution job. Almost anyone can keep a calendar. What this role actually requires is carrying Shawn’s mental load — holding the context, history, and half‑finished threads of his world so he never has to hold them himself. Concretely, that looks like: remembering the shop he mentioned wanting swag from three months ago, without him bringing it up again. Tracking down the thing he was holding — literally or figuratively — last week, before he has to ask where it went. Understanding “no, that’s wrong” with zero further explanation, because you already have enough context to know what he means and fix it. It also means working with your own tools and judgment, not his. Shawn will engage critically with almost anything presented to him as a new system or process — even one he’d genuinely benefit from — so this is not a role for introducing him to a shared dashboard, a new inbox protocol, or a workflow he has to learn. Your infrastructure lives on your side. Success means he never has to think about how any of this gets done. And it means having the standing to redirect him. When Shawn says “this is the project I want you on” and something else is actually on fire, your job is to say so plainly — “that can wait, this can’t, and here’s why” — even when the fire isn’t the thing he’s currently excited about. This is not a role for someone who only executes what they’re told. If you read this and think “I just need clear instructions and I’ll get it done,” this is not the right role for you. If you read this and think “yes, I already do this instinctively for whoever I support,” keep reading. Key Areas of Impact Executive Support & Time Protection (core of the role) Own Shawn’s calendar — scheduling, rescheduling, and defending blocks of deep‑work time Triage his inbox daily: draft responses, flag what needs his attention, handle or archive the rest Book and manage all travel (flights, hotels, visas, itineraries) for work and events Prep Shawn for every meeting — brief him beforehand, take notes, track follow‑ups after Hold full context on his commitments, passing mentions, and half‑finished threads — without needing him to remind or re‑explain Act as gatekeeper: decide what needs to reach Shawn and what doesn’t, using judgment he trusts Scheduling & Logistics Across the Ecosystem Coordinate podcast guest scheduling and logistics for Latent Space (prep docs, calendar holds, follow‑ups) Maintain a shared editorial/events calendar so nothing gets double‑booked or missed Coordinate Shawn’s personal calendar, travel, and commitments around AI.Engineer events Log partnership, sponsorship, and speaking inquiries in a tracking system and follow up on Shawn’s behalf Inbound Triage & Follow‑Through Maintain a single tracking system for inbound requests, commitments, and open loops Follow up on outstanding items so nothing falls through the cracks Flag time‑sensitive or high‑priority items using criteria Shawn sets Draft routine correspondence on Shawn’s behalf when appropriate Route non‑essential questions and requests to appropriate team Meeting & Communication Support Prepare agendas, briefing notes, and background materials ahead of meetings and calls Take notes and distribute clear action items afterward Draft and proofread routine written communications in Shawn’s voice Use AI tools (transcription, summarization, drafting assistants) to move faster — a tool for the job, not a job title What Success Looks Like Shawn’s calendar and inbox never become a bottleneck Travel and logistics run without last‑minute scrambles Meetings happen prepared, on time, with clear follow‑up Shawn rarely has to explain things twice — you already have the context Shawn trusts you completely with his time, his inbox, and his commitments — including trusting you to tell him no Experience & Qualifications Required 5+ years as an Executive Assistant supporting a founder, CEO, or senior executive Proven ownership of a complex calendar, inbox, and travel for a busy principal A track record of anticipating needs and acting on them, not just executing explicit instructions Comfortable working PT hours in a fast‑moving, informal environment Excellent written communication — able to draft clearly in someone else’s voice Familiarity with modern digital tools (Google Workspace, Notion, Slack, scheduling tools) Comfortable using AI tools day‑to‑day to work faster Discretion and trustworthiness with sensitive information and relationships Comfortable in a technical or startup environment — you don’t need to code, but you should be able to follow engineering‑flavored conversation without translation, and be at ease with startup ambiguity (few fixed processes, fast pivots, decisions made without a playbook) Preferred Experience supporting a founder at a startup, media company, or creator‑led business Prior experience working directly with engineers or inside a software company — not just as an enthusiast of AI as a topic Prior startup experience Skills & Competencies Carries context without needing things re‑explained — remembers what he mentioned once, months ago Comfortable overriding Shawn’s own stated priorities when something more urgent surfaces — can say “that can wait, this can’t” and explain why in one sentence Solves problems invisibly, using your own tools and methods, rather than by introducing new systems or processes he has to adopt Anticipation — catches things before they become problems Discretion — trusted with sensitive conversations and relationships Calm, clear communication under time pressure Follow‑through — nothing you own gets dropped Attributes Proactive and detail‑oriented — a thinker, not just a doer Low ego, high ownership — happy doing the unglamorous work that makes everything else possible Trustworthy and discreet Comfortable pushing back on the person you support, respectfully and with reasons Energized by a fast‑moving, varied day rather than a single narrow lane Genuinely motivated by supporting someone else’s success, not building your own platform #J-18808-Ljbffr