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 owns the end-to-end creation of our sales operation in the market, from initial hypothesis to scaled execution. You will architect and run the full sales process, managing full-cycle transactions for both Japanese domestic merchants and global partners who serve our ecosystem. The position requires you to be the primary strategist for market entry, translating high-level company vision into actionable, ground-level sales initiatives. You will build key strategic partnerships that integrate Outpost's infrastructure into existing platforms and expand our commercial reach across new revenue channels. As a founding member, you will directly collaborate with the CEO and the founding team to refine our go-to-market approach and validate product-market fit in Japan. This role demands a proactive, entrepreneurial mindset capable of thriving in early-stage ambiguity and delivering significant, measurable impact in the fintech and cross-border commerce sectors. You will be the definitive voice for sales in Japan, shaping narratives and driving adoption of our cross-border commerce infrastructure.

Key facts

What you'll do

Identify and develop strategic B2B2B partnerships where Outpost's infrastructure can be embedded within existing platforms, creating scalable revenue channels and extended market reach.

Execute outbound prospecting campaigns, including cold outreach, targeted email sequences, and advanced lead research using AI tools to build a multi-stage, high-quality sales pipeline.

Synchronize closely with internal product, marketing, and customer success teams to ensure sales activities reflect company objectives and accurately represent our evolving product suite.

Configure, manage, and analyze the CRM pipeline to track every opportunity, forecast accurately, and provide leadership with data-driven insights for strategic refinement.

Monitor and interpret market trends, shifting customer requirements, and competitive movements within Japan's cross-border commerce and fintech sectors to inform positioning.

Leverage AI instruments such as Claude and autonomous AI agents to conduct account research, enrich leads, craft personalized outreach, and accelerate proposal development.

Provide direct feedback to product teams based on real-world client interactions and market intelligence to influence Outpost's market entry and growth strategies in Japan.

Represent Outpost at industry gatherings, conferences, and networking forums to establish brand authority and strengthen our reputation in Japan's fintech and commerce communities.

Create, document, and iterate on sales processes, playbooks, and best practices to establish a repeatable framework for scalable expansion.

Champion a customer-obsessed mindset, ensuring every prospect and client experiences a professional, positive, and value-driven sales journey from first contact to closure.

Take personal accountability for assigned sales quotas, employing a bias for action and a rigorous, results-oriented approach to exceed performance goals.

Utilize advanced AI-driven research and automation capabilities to optimize daily sales activities, improve outreach efficiency, and shorten deal cycles.

Maintain strict data hygiene and pipeline discipline within CRM systems, ensuring accuracy, transparency, and reliability for forecasting and planning.

Cultivate resilience and patience in outreach initiatives, prioritizing long-term trust and strategic relationship creation over immediate transactional wins.

Requirements

Demonstrate business-level fluency in both Japanese and English, conducting the entire sales cycle in Japanese while collaborating seamlessly in English with global teams.

Prove the ability to close complex, full-cycle B2B sales, progressing from initial prospecting and discovery through negotiation, legal review, and final contract execution.

Show a documented history of building and managing extensive sales pipelines using both inbound and outbound methods, consistently meeting or surpassing set targets.

Explain intricate product details related to tax regulations, payment processing, compliance frameworks, and liability limitations with clarity and persuasive conviction.

Thrive in early-stage or undefined operational environments, transforming ambiguous requirements into concrete strategies and actionable execution plans.

Exhibit a proactive, self-starting attitude dedicated to improving and owning sales methodologies instead of merely following established procedures.

Utilize AI instruments such as Claude and AI agents to enhance sales productivity, including research, communication, and documentation tasks.

Possess outstanding communication and interpersonal abilities, forming rapid trust and effective relationships with diverse stakeholders.

Organize multiple concurrent opportunities with meticulous attention to detail, ensuring thorough follow-through and accurate forecasting.

Show resilience and persistence in outreach activities, emphasizing long-term relationship development and the creation of ongoing client value.

Work autonomously, taking ownership of sales initiatives and succeeding in a fast-paced, dynamic startup environment with minimal direct supervision.

Commit to staying current with trends, regulations, and innovations in cross-border commerce, fintech, and Japan-specific financial policies.

Nice to have

Prior experience selling Merchant of Record solutions, tax compliance platforms, or cross-border financial products, particularly within fintech or payments.

A sales history targeting or operating within the Japanese market, with established local contacts and an understanding of regional business etiquette.

A genuine interest or background in fintech, cross-border commerce, or adjacent industries that demonstrates deep enthusiasm for the sector.

Knowledge of Japanese business culture and relationship-building protocols to facilitate smoother negotiations and partnership development.

Experience managing international client portfolios and navigating cross-cultural communication complexities with ease.

Practical notes

This position is based in Tokyo, Japan, and requires consistent on-site presence at the company office.

You will work closely with teams located in London and Amsterdam, necessitating effective communication across multiple time zones and cultural contexts.

The role offers significant ownership and direct access to the CEO, providing a unique opportunity to directly influence the strategic direction of the company in Japan.

To apply, please include details of a successfully closed deal, your strategic approach for the Japanese or APAC market, and an optional outbound message written in Japanese.

The company operates in a dynamic environment where individual contributions will have a direct and measurable impact on overall business success.