Executive Assistant

🌍 About Outpost

Global expansion is broken. Without a local entity, conversion rates fall, costs rise, and compliance gets messy. Outpost fixes it.

Outpost is your modular back office for global commerce. Pick only what you need - tax, payments, treasury, or operations - and unlock new markets without the overhead. Sometimes we act as Merchant of Record, taking on tax and compliance risk. Other times, we give you the tools to do it yourself.

Sell anything, anywhere. Without compromise.

🧠 The Role

We're hiring a second Executive Assistant to support our CEO.

We already have an EA, and she isn't going anywhere. You'll report to the CEO and work alongside her: she keeps inbound, customer routing and the investor-facing side, takes diary, travel, logistics, internal admin, and hiring coordination. You'll join to take a defined set of workstreams off that plate.

Roughly 70% of this role is executive support. The other 30% is hiring - and that's where the leverage is. We run a five-stage interview loop across engineering, ops, product, GTM and tax, hiring around two people a month. Someone needs to own the machinery: scheduling across five calendars and four countries, keeping candidates warm, chasing feedback, making sure nobody good goes cold because a diary didn't line up.

This is a role for someone early in their career who is unusually organised and wants to learn how a company actually gets built. You won't be handed a finished process. You'll be shown how we do things today, and expected to make it better.

🧩 What You'll Do

Own the CEO's diary and logistics

• Run scheduling day to day - booking, moving, protecting focus time, resolving clashes before they become problems

• Book and manage international travel, and rebuild it when a flight moves

• Prepare meeting packs: who's in the room, what they want, what happened last time

• Track and chase the follow-ups nobody wrote down

Do the work he never sees

• The highest-value work here is invisible. He shouldn't know it happened - he should just find the day went smoothly

• Fix problems before they reach him: the double-booking, the missing dial-in, the visa that needed renewing

• Do the quiet prep - background on a person he's m