Head of Sales - Japan

Company Description At Square, our purpose is to build tools that help sellers start, run, and grow their businesses. What began as payments has evolved into a broad ecosystem of commerce solutions — including software, banking, financial services, and omnichannel capabilities designed to work together seamlessly. Japan represents one of the most strategic growth opportunities for Square globally. It is a complex, highly competitive market with enormous potential across commerce, hospitality, retail, and services. We believe the opportunity ahead is significant — but winning in Japan will require bold commercial leadership, operational intensity, and a relentless focus on execution. We are entering the next phase of growth in Japan with the ambition not just to participate in the market, but to build a category-defining business. The Role Square is seeking a Head of Sales for Japan to build and rapidly scale our commercial business in-market. This leader will be responsible for accelerating revenue growth, increasing market penetration, and building a high-performing sales organization capable of winning at scale in one of the world’s most important and demanding commerce markets. This is a builder role for a commercially driven operator who thrives in fast-growth environments and knows how to turn opportunity into execution. The ideal candidate combines deep enterprise and SMB commercial expertise with strong knowledge of the Japanese market, customer expectations, competitive landscape, and a strong bias for action. They know how to build strong teams, drive urgency, unlock new growth vectors, and push organizations to move faster and execute at a higher standard. This role requires a leader who is highly motivated, commercially aggressive, and execution-oriented — someone who embraces ambitious goals, operates with intensity, and can help establish Square as a market leader in Japan. What You’ll Lead Growth & Commercial Expansion • Own overall revenue growth and market expansion strategy for Japan. • Build and execute an aggressive growth plan across SMB, mid-market, enterprise, and strategic verticals. • Identify and unlock new commercial opportunities, partnerships, channel strategies, and scalable go-to-market motions. • Develop and scale a high-performing channel and partner sales strategy to accelerate market penetration and revenue growth. • Build strong relationships with strategic channel partners, resellers, ISVs, and ecosystem players to expand Square’s reach and influence in Japan. • Drive pipeline generation, conversion, and expansion with a strong focus on execution velocity and measurable outcomes. • Increase competitive win rates and establish Square as a differentiated leader in the Japanese market. • Develop clear market segmentation and prioritization strategies to maximize growth and resource allocation. • Build scalable commercial motions that support rapid long-term expansion in Japan. Sales Leadership & Operational Excellence • Lead and scale a high-performing, multi-layered sales organization across Japan. • Create a culture of accountability, urgency, resilience, and execution excellence. • Raise the talent bar through strong hiring, coaching, performance management, and leadership development. • Improve sales productivity, forecasting accuracy, and operational rigor across the organization. • Build repeatable sales motions and operating mechanisms that enable scale. • Drive disciplined execution while maintaining agility in a fast-moving market. Market Leadership & Strategic Influence • Serve as one of Square’s senior commercial leaders in Japan and represent the voice of the market internally. • Partner closely with Product, Marketing, Partnerships, Customer Success, and Gl