Regional Sales Manager

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

The Role

Square's mission is to power all the ways small businesses do business, helping Australian Sellers operate more efficiently, grow confidently, and unlock new opportunities. As we continue scaling across Australia, we're looking for a Regional Sales Manager to lead and support a network of self-employed, Independent Consultants (ICs) who drive adoption of Square's payments and business solutions across the SMB market.

In this role, you'll own the performance and development of your regional IC network, working hands-on in the field to help them win more business and close more deals. You'll be the bridge between Square and your ICs, coaching them toward excellence, modeling effective sales behaviours, and ensuring they're equipped to represent the full Square ecosystem across multiple verticals including retail, hospitality, services, and more.

This is a dynamic, field-based role designed for a sales leader who thrives on the ground, working shoulder-to-shoulder with ICs to drive results. You'll balance strategic planning with tactical execution, using your payments and POS expertise to unlock opportunities and your coaching skills to elevate IC performance. The ideal candidate will bring an established network of agents they've worked with previously, enabling a fast start and immediate impact.

This role requires regular travel across your assigned region. You'll work remotely within Australia with the flexibility to structure your time around field visits, coaching sessions, and regional meetings.

You Will

• Lead and develop a network of self-employed Independent Consultants across your region, providing ongoing coaching, training, and field support to maximize their performance


• Work in the field regularly to accompany ICs on sales calls, model consultative selling techniques, and help close deals—especially complex or high-value opportunities


• Leverage your established network of independent sales agents to rapidly build and scale your IC team, bringing proven performers who can hit the ground running


• Drive seller acquisition across the SMB market, focusing on multiple verticals and promoting the full Square ecosystem including payments, POS, online tools, and business management solutions


• Develop and execute a regional sales plan that sets clear goals, tracks regional performance, and adjusts tactics based on real-world results and market feedback


• Analyze sales performance using pipeline data, conversion metrics, and activity reports to identify coaching opportunities and optimize IC effectiveness


• Provide reliable forecasts and performance updates to leadership, highlighting wins, challenges, and insights from the field


• Capture market intelligence from your ICs and prospects about local SME needs, competitive dynamics, and emerging opportunities to inform strategy


• Ensure alignment between ICs and Square's standards, values, and go-to-market approach while respecting their independence as self-employed professionals

You Have

• 5+ years of experience in a similar field sales leadership role, with a proven track record of managing self-employed or independent sales agents (experience in the Australian market strongly preferred)


• Deep industry expertise in payments and POS solutions, with the ability to speak credibly to SME pain points and demonstrate product value across diverse business types


• An established network of independent sales agents or consultants you've worked with previously and can bring into this role to accelerate team building and performance


• Strong coaching and leadership skills, particularly in environments where you influence through expertise and support rather than direct authority


• Consultative sales excellence—you've personally closed complex deals and can model best practices for your ICs in the field


• Analytical capabilities to interpret performance data, identify trends, and translate insights into actionable coaching and strategy adjustments


• Exceptional interpersonal skills to build trust and drive alignment with independent contractors who may be working with multiple partners


• A results-oriented mindset with experience consistently meeting or exceeding sales targets in fast-paced, high-growth environments


• Comfort with ambiguity and the entrepreneurial drive to build and scale a regional operation with autonomy and accountability

Nice to Have:

• Experience selling across multiple SMB verticals (retail, hospitality, professional services, etc.)


• Knowledge of the Australian SME landscape, regional market nuances, and local business needs


• Experience with commission-based or performance-driven sales models


• Familiarity with fintech, SaaS, or technology solutions for small businesses