Sales

About Outpost

Outpost is the infrastructure layer for cross-border commerce. We become the legally liable entity for tax, payments and customs wherever our merchants sell next. Series A, backed by Ribbit Capital and Better Tomorrow Ventures.

 

You will work alongside one of the strongest operating teams in fintech. Our founders and engineers built and scaled the products you already know: Revolut, Adyen, Airwallex. You will be plugged straight into that team, learning how a serious company is built from the inside.

We are building our commercial function from the ground up. We want a closer on the ground in Tokyo who can build the playbook with us, and sell it in Japanese and English.

 

The role

You own full-cycle sales, end to end. You prospect, you qualify, you close. You report to the CEO and work directly with the founders.

 

Japan is one of our sharpest openings: proxy platforms, D2C brands and app studios selling out of Japan into Europe and the US, all hit by cross-border tax, payments and customs friction. You are our person in-market. You will own that motion and sell to those merchants in their own language, in their own time zone.

 

This is not an account-management seat waiting for inbound. It is a build-the-engine role dressed as a sales role. You close the deals, and you shape how we sell: the pitch, the positioning, the materials. You will sell direct to merchants and help develop B2B2B channels where Outpost powers partner platforms.

 

What you'll own, examples:

1. Pipeline. Build your own book from scratch. Outbound to Japanese and global merchants expanding cross-border, plus the inbound we generate. You do not wait for leads, you make them.

2. Full-cycle deals. Run discovery, demos and negotiation in Japanese and English. Navigate multiple stakeholders and complex tax, payments and compliance requirements to close.

3. The Japan / APAC motion. Own it end to end. Identify the accounts, build the account-based plays, and be the commercial owner of the market while carrying global deals alongside it.

4. Sales materials. Refine the pitch decks and one-pagers based on what actually lands in calls. Localise the story for Japanese buyers where it moves deals.

5. Positioning and proof. Feed field objections back into messaging. Turn closed deals into the case studies and proof points that close the next one.

6. B2B2B channels. Develop partnerships where Outpost is embedded in a platform that already serves your target segment.

 

What we test for

• Business-fluent Japanese and English. You run the full sales cycle in Japanese and operate with the team in English.

• You are AI-native by instinct. You use Claude and agents to do the grunt work of selling: research an account, enrich a lead, draft a personalised outbound sequence, prep a call, turn a scope into a first-cut proposal. The point is leverage - AI does in minutes what eats a rep's afternoon, so you spend your time in front of buyers, closing. You run a bigger pipeline than one person should be able to, because you have built the machine that feeds it.

• You have closed before. Full-cycle B2B sales, prospecting through signature, ideally in fintech, payments or e-commerce infrastructure. Show us a deal you owned.

• You build your own pipeline. Inbound and outbound. You do not observe, you ship.

• You can hold a complex product. Tax, payments, compliance, liability. You learn fast and explain it simply, in both languages.

• Fluent in ambiguity. Early-stage means no playbook. You turn a vague gap into a working motion.

• Bias for action. You move fast, close fast, and want to shape how we sell rather than just execute it.

Nice to have: sold Merchant of Record, tax, compliance or cross-border products; experience selling into or out of Japan; an interest in fintech.

 

What you'll get

• Real ownership of real deals from week one, and your own market to run.

• Direct access to the CEO and founding team, and a front-row seat at a fast Series A company.

• Equity and salary, low politics, high output. A reference and a network if you close.

 

How to apply

No cover letter. Send us:

(1) a deal you owned, start to finish, and what you did to win it;

(2) one line on which Japanese or APAC segment you would go after first, and how;

(3) bonus - a short outbound message you would send a target merchant, in Japanese. Whoever sells gets the call.

 

Location: Tokyo. You are close to your market, and connected daily to the London and Amsterdam team.