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 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-hands, offsites, 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 offsite 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 escalate, 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 internal operations too

Not a pure recruiter role - hiring is a third of the job, not the whole of it

Not a role for someone who needs defined processes and hierarchy to be effective

Not a stepping stone you can coast through. The exposure is real, and so is the pace

🚀 Why This Role Is Different

Most assistant roles are about keeping someone else's life tidy. This one is about making a company move faster.

You'll own hiring coordination, which at our stage is one of the highest-leverage things we do — the people you help bring in will shape what Outpost becomes. And you'll get a front-row view of a Series A fintech being built, with two people above you invested in teaching you how it works.

We expect whoever is in this role to grow rapidly, and we'll back you every step of the way.

🦾 Outpost Team

Our team were leaders at Revolut, Airwallex, Adyen, Sumup and Wayflyer - and we're backed by top-tier investors who have built or backed some of the world's leading fintechs.

🧾 What We Offer

Equity and salary in a well-funded startup

Ability to own your work and move fast

World-class training from operators who've scaled globally

A global mission with real impact

Low politics, high output

Chance to grow into a senior role fast

A culture of builders, not talkers

🌎 Reach Out

Learn more

Outpost Culture

Outpost founder

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