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 meeting, what was agreed last time, the numbers checked before a deck goes out
- Anticipate. If a trip is booked, the transfer, the dinner and the buffer around the flight are already handled
- The fewer questions he has to ask you, the better you're doing the job
Own hiring coordination
- Run scheduling across the full interview loop - five stages, multiple interviewers, several time zones
- Keep the pipeline clean: trackers, interview feedback, stage‑by‑stage conversion
- Build target lists for open roles and help manage outreach
- Be the candidate's point of contact - fast, warm, human. How we treat candidates is how we're judged
- Coordinate offers, references, contracts, start dates, and new‑hire onboarding logistics
Keep the company running
- Support board and investor prep alongside the CEO, Chief of Staff and our senior EA
- Help run internal comms: all‑heads, off‑sites, company updates
- Manage supplier, tooling and expense admin so nobody else has to think about it
- Spot the recurring problem and fix it permanently rather than solving it again next week
Example Projects
- Rebuild a full week of CEO travel in an afternoon after a fundraising meeting moves
- Take time‑to‑offer from three weeks to ten days by fixing scheduling and feedback bottlenecks
- Build the candidate tracker that shows conversion at every interview stage, and run it weekly
- Own the logistics for a board meeting: pre‑reads, agenda, materials, follow‑ups
- Organise a company off‑site for a team split across London, Amsterdam and beyond
- Write down how you do your job so the next person can pick it up in a week
What We’re Looking For
Ideal background:
- 1-3 years in an EA, team assistant, recruiting coordinator or ops support role - ideally at a startup or fast‑growing tech / fintech company
- Any recruiting coordination exposure is a plus, but we'll teach it if you're quick
- Comfortable in a company without much process, because you've worked in one before
- Fluent with modern tooling (Notion, Slack, Linear, ATS, scheduling tools and AI) and quick to pick up new ones
- Excellent written English. You'll write on the CEO's behalf
Signals we care about
- Ridiculous bias for action - you solve, not observe
- Extremely organised, and visibly so. Nothing gets dropped, nothing needs chasing twice
- Strong EQ - you know how to read a room, a candidate, or a blocker
- Sound judgement - you know what to decide yourself and what to elevate, and you sit on neither
- Discreet. You'll see comp, term sheets and candidate conversations before most of the team
- Curious and resourceful - you can figure anything out
- You improve what you touch. The second time you do something, it should be faster than the first
What this role is not:
Not a diary-only role - you'll own hiring, onboarding and inte
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