Remote Field Sales Leader

Square

Square is looking for a Sales Leader to build and manage a high-accountability field sales team, focusing on coaching Territory Account Executives.

Last checked on July 16, 2026. We may earn a commission when you click through.

The opportunity to lead and shape a sales team at Square is compelling, especially for experienced sales leaders. However, candidates should be prepared for a demanding environment that prioritises performance metrics.

✓ Remote work flexibility ✓ Strong focus on team development ✓ Reputable company with innovative solutions

Remote Field Sales Leader

Square

Updated 5 days ago

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Queensland Remote

About this role

Square is looking for a Sales Leader to build and manage a high-accountability field sales team, focusing on coaching Territory Account Executives.

About the Company

Square is a global financial services and digital payments company, known for its innovative solutions for businesses.

Key Highlights

✓ Remote work flexibility
✓ Focus on coaching and development
✓ High-accountability environment
✓ Opportunity to scale a sales team
✓ Requires over 8 years of sales experience

💡 Honest Take: This role is ideal for seasoned sales professionals who thrive in leadership positions and value a culture of accountability.

Pros

✓ Remote work flexibility
✓ Strong focus on team development
✓ Reputable company with innovative solutions
✓ Chance to lead and influence
✓ High accountability fosters growth

Cons

✗ Requires significant experience (8+ years)
✗ Performance culture may be stressful
✗ Remote role may lack in-person support
✗ High expectations on KPIs
✗ Limited salary transparency

Best For: Ideal for professionals who are motivated by performance metrics and enjoy coaching others.

Watch Out: The demanding performance culture might not suit everyone, particularly those preferring a more relaxed work pace.

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What Customers Say

Feedback from employees highlights a supportive culture but notes the intense focus on performance can be stressful.

Expert Review

Leading a sales team at Square presents a unique opportunity for seasoned professionals. The focus on accountability and performance metrics can drive team success but may also create pressure. We noted that the emphasis on developing Territory Account Executives highlights the company's commitment to growth.

Square for its innovative approach to digital payments, which can be appealing for those passionate about technology in sales. However, candidates should be aware of the high expectations surrounding KPIs, which could lead to a challenging work environment.

The remote aspect of the role is allowing for flexibility in work-life balance. Yet, potential candidates should consider that being remote may limit immediate support and camaraderie typically found in a physical office. Overall, this position is best suited for those ready to embrace challenges and drive success in a fast-paced sales environment.