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About the Role

As an SME Account Executive at Square, you will convert high-quality, interested leads into long-term customers while proactively sourcing opportunities to maintain a robust pipeline. You will be central to our growth engine, operating in a fast-paced, metrics-driven environment designed for high achievers. This role is for individuals who take initiative, avoid excuses, and maintain high standards.

Responsibilities

• Manage the full sales cycle from initial outreach to closing deals with SME merchants across various industries.
• Engage and convert a steady stream of interested leads from marketing, partnerships, or inbound interest.
• Generate a significant portion of your pipeline through proactive prospecting, identifying new opportunities, and creating demand.
• Act with diligence, managing time and priorities effectively in a high-volume environment.
• Understand customer challenges and provide consultative, value-based solutions with measurable impact.
• Collaborate with cross-functional teams (Onboarding, Product, Marketing, Support) to ensure a seamless customer experience.
• Track and forecast your pipeline accurately in Salesforce, using data and metrics to drive performance.
• Consistently meet and exceed monthly and quarterly revenue targets.
• Continuously improve conversion rates, contract values, and activity levels.
• Navigate complex negotiations and overcome obstacles.

Requirements

• 1-2 years of remote, full-cycle sales or contract negotiation experience, ideally in a fast-paced SaaS, payments, or SME-focused environment.
• Proven ability to exceed quotas and close deals in short sales cycles with high transaction volumes.
• Strong communication skills via phone, video, and written channels, establishing trust and driving deals forward.
• A hunter mentality with a disciplined prospecting approach to build and accelerate pipeline independently.
• Curiosity and empathy to understand customer businesses, uncover needs, and confidently propose solutions.
• Ability to thrive in ambiguity, demonstrating motivation and a desire to learn and grow.
• Proficiency with a CRM (Salesforce or equivalent) and a data-driven approach to activity management.
• High standards for yourself and your team, celebrating wins, sharing best practices, and raising the bar for others.
• Ability to sell in both French and English.

Skills

• Sales
• Negotiation
• SaaS Sales
• Payments
• CRM
• Salesforce
• Prospecting
• Lead Generation
• Pipeline Management
• Communication
• Problem Solving
• Consultative Selling
• French
• English

Location

• Canada

Work Type

• Remote

Experience Level

• 1-2 years

Salary/Compensations

• $86,000—$129,000 CAD

Benefits

• Remote work
• Medical insurance
• Flexible time off
• Retirement savings plans
• Modern family planning

About the Company

• Square has evolved since its inception in 2009, moving beyond simple payment processing to developing integrated, omnichannel software solutions. These tools help merchants sell online, manage inventory, offer buy-now-pay-later options, schedule appointments, build customer loyalty, and manage employees. Financial services tools are integrated into the point-of-sale system, providing merchants with access to business loans and cash flow management. Afterpay enhances Square's goal of providing omnichannel tools that drive significant value and growth, enabling merchants to attract new buyers, increase order volume, and scale effectively. Square partners with businesses of all sizes, from startups to large enterprises, supporting their growth with evolving solutions. The company is building a significant and sustainable business, empowering merchants globally.
• Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Our brands unlock different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

Equal Opportunity

• We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.