Sales / Go-to-Market

About the role

Outpost is seeking a founding Sales professional to establish and grow our commercial presence in Japan. This role involves building the sales process from the ground up, focusing on full-cycle sales to Japanese and global merchants. You will be instrumental in shaping our market strategy and closing deals for our cross-border commerce infrastructure.

Key facts

What you'll do

• Generate new business by building a pipeline from scratch, targeting Japanese and international merchants expanding globally.
• Manage the entire sales cycle, from initial discovery and demonstrations to complex negotiations in both Japanese and English.
• Develop and execute the sales strategy for the Japan and APAC markets, identifying key accounts and crafting tailored approaches.
• Refine sales materials, including pitch decks and one-pagers, based on direct feedback from client interactions.
• Translate field insights into improved messaging and transform successful deals into compelling case studies.
• Explore and develop B2B2B partnerships where Outpost's solutions can be integrated into existing platforms.

Requirements

• Business-level fluency in both Japanese and English, enabling full sales cycle execution in Japanese and internal team collaboration in English.
• Demonstrated ability to close full-cycle B2B sales, from prospecting to contract signing.
• Proven track record of building your own sales pipeline through both inbound and outbound efforts.
• Capability to understand and articulate complex product details related to tax, payments, compliance, and liability in simple terms.
• Comfort operating in an ambiguous, early-stage environment, turning undefined needs into actionable strategies.
• Strong bias for action, with a desire to actively shape sales processes rather than just execute existing ones.
• Instinctive use of AI tools for sales tasks like account research, lead enrichment, personalized outreach, and proposal drafting.

Nice to have

• Experience selling Merchant of Record, tax, compliance, or cross-border products.
• Prior sales experience targeting or operating within the Japanese market.
• An interest in the fintech industry.

Skills & tools

• Claude (AI)
• AI agents

Practical notes

This role offers significant ownership and direct access to the CEO and founding team. To apply, submit details of a deal you closed, your strategy for a Japanese/APAC segment, and an optional outbound message in Japanese. You will be connected daily with teams in London and Amsterdam.