AI-Native Executive Assistant

We're hiring an AI-Native Executive Assistant for a fast-growing, retention-first e-commerce marketing agency for Shopify DTC brands — one of the Klaviyo Elite Partners worldwide, and also a Shopify Plus Partner. The founder also runs a venture-backed startup building an AI operating system for retention agencies and the brands they serve.

This role exists because the founder is running two companies and currently doing his own executive support inside AI tools. You will take that over, and then do something most assistants never get to do: build the systems that make your own job smaller every quarter. This is not a calendar job with a chatbot bolted on. Half of your week is world-class executive support. The other half is engineering that support out of existence.

The Job

• Calendar and inbox as a system: full control of scheduling across two companies, triage on email and Slack, and a defensible answer at all times to "what actually needs him today."
• Meeting exhaust to closed loops: every call runs through Granola or Fireflies. You turn transcripts into action items, owners, and Asana tasks the same day, then chase them to done instead of filing them.
• Pre-call briefing: no external meeting starts cold. Partner calls, client escalations, investor conversations, and candidate interviews each get a short brief with attendee background, account history, and the three things that need to come out of the room.
• Cross-tool status retrieval: pulling a real answer out of HubSpot, Gmail, Slack, and Fireflies at once. "Where does this deal stand" should take you ten minutes and produce something forwardable.
• Correspondence in his voice: follow-ups, nudges, partner updates, close-out notes, and referral intros. You draft, he edits, and over time he edits less.
• Travel and events: conference logistics for the team. You will build a standing preferences brief in your first month so no booking decision ever gets researched from scratch twice.
• Deliverable production: one-pagers, briefing docs, case studies, and partner assets built on the brand system and produced fast enough to be useful.
• Automation build: this is the half that makes the job different. You will build Claude skills, n8n workflows, and MCP-connected pipelines that absorb recurring work: meeting notes into Asana, invoice reconciliation, notification triage, reporting pulls, onboarding sequences.
• An automation ledger: you track what you built, what it replaced, and how many hours per month it reclaimed. This is how your performance gets measured alongside the executive support itself.
• Venture-side administration: entity filings, investor and advisor correspondence, document management, and vendor coordination for the founder's startup, handled with the discretion that implies.

You're a Fit If

• You have supported a founder or senior executive for at least two years, and you have handled the unglamorous end of it: expense reports, visa paperwork, canceled flights, awkward reschedules.
• You have already built something with AI that another human being still uses. A workflow, an agent, a script, a custom GPT, an n8n automation. You can show it and explain why you built it that way.
• You work with Claude or an equivalent tool every day, not occasionally.
• You write English at a native or near-native level. Much of your output goes to clients, partners, and investors under his name.
• You work United States Eastern business hours.
• You are fluent in Asana, HubSpot, Slack, and Google Workspace, and you can teach yourself n8n and Supabase without a training plan.
• You handle compensation data, cap table documents, client contracts, and candidate feedback without anyone reminding you to.
• When you are unclear, you ask once, precisely, and then move. You do not stall and you do not guess.

Not a Fit If

• You need a task list handed to you. Most of what you will own, you will find yourself.
• You think "AI-native" means you use ChatGPT to polish emails. We mean you build things.
• Open-ended research tasks tend to expand to fill whatever time is available. A hotel booking is a thirty-minute task, and if it takes three hours we have a problem.
• You need consensus and a long runway before you act.
• You want the same job a year from now. Every task you master, you should be trying to delete.
• Automating away part of your own work feels like a threat to your job security rather than the point of it.
• You are more comfortable taking care of the team than protecting the founder's time. Both matter, but this role is unambiguously the second one.

What You Get

• Direct, high-trust partnership with a founder running two companies at once.
• Real authority over automation — you build the workflows, own the ledger, and get the credit for hours reclaimed.
• Fully remote, on a team distributed across Latin America, running on EOS.
• A front-row seat inside a top e-commerce retention agency serving DTC brands doing $2M+ in annual revenue.

Our Operating Principles

• Accountability: see it, own it, solve it, do it
• Proactivity: don't wait for direction, act
• Ownership: ask "what else can I do," not "is this my job"
• Communication: clear, direct, and frequent
• Curiosity: stay hungry, embrace change, build better
• Gratitude: notice the win and say so
• Care: for clients, teammates, and yourself

Apply here: https://forms.clickup.com/9011940787/f/8cjekdk-3311/PTSY0TJR3NUUHL5KJ6

APPLICANTS WILL ONLY BE CONSIDERED IF THEY FORMALLY APPLY USING THE LINK ABOVE. ANY DIRECT EMAILS OR PHONE CALLS REGARDING THIS ROLE WILL RESULT IN AUTOMATIC DISQUALIFICATION.

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