Head of Sales

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 Global Sales leaders to accelerate growth and unlock new opportunities.
• Influence regional and global strategy through strong market insight and customer understanding.
• Build strong executive-level relationships with key customers, partners, and ecosystem stakeholders.
• Help shape Square’s long-term market position and brand presence in Japan.

Cross-Functional & Global Collaboration

• Partner closely with international sales and GTM leaders to share best practices and accelerate learning across markets.
• Ensure Japan both benefits from and contributes to Square’s global commercial strategy and innovation.
• Collaborate effectively across time zones, functions, and cultures to drive alignment and execution.
• Balance strong local market judgment with global operating standards and strategic priorities.

We’re Looking For

• 15+ years of sales and commercial leadership experience, including significant experience scaling high-growth businesses.
• Proven track record of rapidly growing revenue and taking market share in highly competitive environments.
• Strong builder mentality with experience creating and scaling organizations, GTM motions, and commercial infrastructure from the ground up.
• Deep commercial expertise across complex sales environments, including SMB, mid-market, enterprise, strategic partnerships, and channel sales.
• Strong experience building and scaling channel sales, strategic partnerships, and indirect go-to-market motions in complex and competitive markets.
• Proven ability to leverage partner ecosystems to accelerate growth, increase distribution, and drive commercial scale.
• Demonstrated ability to lead through ambiguity, move with urgency, and drive operational discipline at scale.
• Strong executive presence with the ability to influence cross-functional and global stakeholders.
• Experience operating within global organizations and navigating cross-cultural environments.
• Deep understanding of the Japanese commerce, payments, SaaS, or technology landscape strongly preferred.
• Fluency in Japanese and English preferred.

Why This Role Matters

Japan is one of Square’s most important long-term growth markets globally. The opportunity is substantial, but success will require a leader who can build aggressively, execute decisively, and scale a world-class commercial organization.

This role is not about maintaining the status quo. It is about accelerating growth, increasing market share, building competitive advantage, and creating a durable commercial engine for the future.

The right leader will combine strategic thinking with operational intensity. They will build strong teams, move quickly, raise standards, and help establish Square as a market leader in Japan.

Zone A Salary Range: 223328.0 - 334992.0 USD
Zone B Salary Range: 223328.0 - 334992.0 USD
Zone C Salary Range: 223328.0 - 334992.0 USD
Zone D Salary Range: 223328.0 - 334992.0 USD
Canada Zone A Pay Range: 218064.0 - 327096.0 CAD
Canada Zone B Pay Range: 218064.0 - 327096.0 CAD